Who loves a good roller coaster? There is not a better analogy for the 2021-22 Tottneham Hotspur season than that of a roller coaster, and I am here to guide you through the roller coaster that was this season. My name is Dustin Gentile, and over the next few weeks, I will be here to give you my take on the 2021-22 Tottenham Hotspur season. On Tuesdays and Thursdays, I will be bringing you my take on the best goals, most exhilarating matches, the biggest moments, and brightest stars from the season that was 2021-22. If you missed last week’s countdown of the top goals of the season, you can find part one here and part two here.
Without much further ado, let’s look at this week’s list…
Matches of the Season (#5-1)
If you missed part one of my countdown of the top matches of the season, be sure to check it out here. Just a reminder in creating this list, I judged all of the matches on the following criteria: the impact the match had on the season, the riveting moments of the match, and the quality of the match itself. Let’s get back to our countdown…
#5 – 5/7/22 – Liverpool 1 – Tottenham 1

With just four matches remaining on the season, Tottenham Hotspur knew the task ahead of them if they hoped to claim a spot in next season’s Champions League. With a MASSIVE North London Derby on the horizon, the task ahead would not be easy. If Antonio Conte’s men wanted to arrive at that match with everything to play for, they could ill afford a loss against at Anfield to a Liverpool team also looking to keep pace in a race of their own. The Reds were looking to make history as they pressed on towards a historic quadruple winning season. Sitting just a point behind league leaders Manchester City, Jurgen Klopp’s team also faced similar pressure as they hoped to avoid a debilitating loss. It would set the stage for one of the most impactful matches in the 2021-22 Premier League season.
Liverpool had the best chance of the opening half in the 28th minute when a cross into the box intended for Jordan Henderson was accidentally headed back towards goal by Ryan Sessegnon forcing Tottenham captain Hugo Lloris to tip the ball away from a cutting Mo Salah to clear the danger. The hosts would have another decent chance as Thiago Alcantara would fire in a cross to recent signing Luis Diaz, but Harry Kane would also rise to meet the ball and take the sting out of the header, which allowed Lloris to gather the chance. Spurs would also find a quality chance late in the first half that nearly found the back of the net. After the official allowed Spurs to play an advantage, Eric Dier would spring Spurs out on the counter with a quick pass to Harry Kane. Kane would then buy some time and space near the halfway line before connecting with a streaking Son Heung-min who would also look to find an opening as he approached the Liverpool box. That opening came in the form of Pierre-Emile Hojbjerg who collected a pass from the South Korean and turned his sights on goal with a low laser from about 27 yards out that would beat a diving Alisson but hit the outside of the left post. It would have been a sensational opening goal for the Danish destroyer, but the first half came to an end just as it began: scoreless. While the hosts would hold an advantage in possession (64%-36%) and total shots (11-3), Spurs’ counter attack and strong defense had kept them alive without too many signs of danger.
It would not take very long for business to pick up in the second half. Hugo Lloris would spring Spurs into attack with a low boot that found Emerson Royal just short of the halfway line before the Brazilian would send a looping diagonal into the Liverpool end that would find Harry Kane in prime position. Kane would use a slick dribble to avoid Trent Alexander-Arnold as a cutting Son would draw the attention of Ibrahima Konate and Andrew Robertson, which left wingback Ryan Sessegnon all alone on the left hand side. Kane would slide a pass to the cutting Sessegnon at the six yard box. Had the English international thought to take the first touch on his right foot, he could have scored his first goal of the season; however, Sess made the smart play and took his first touch with his left foot to pick out Sonny all alone inside the area to put the North London club ahead 1-0 on the evening with a tidy finish. It was an incredible team goal to keep Tottenham’s Champions League hopes very much alive. In my opinion, this was the match that cemented Ryan Sessegnon’s spot in Conte’s side. Injuries had plagued the England international’s career in North London to this point, but the 21 year old had finally started to turn the corner and assert himself as a force for this team.
Spurs would then face the full onslaught of the Liverpool attack in the final 34 minutes of play with Liverpool seeing the vast majority of the possession and chances in that second half. One of the defensive highlights of that half came in the 73rd minute when a Liverpool counter attack found the foot of the Premier League’s leading goal scorer (at the time), Mo Salah. The Egyptian would beat his first man and fire a quick shot at the Tottenham goal, but an incredible lunging effort by Ben Maldini … sorry, Ben Davies preserved Spurs’ lead. While the Reds would eventually find an equalizer in the 74th minute to send both teams home with a point, Antonio Conte’s men showed that they were not going to back down from any team. The result would also set up a do-or-die North London Derby five days later, but we will come onto that match later in our countdown.
#4 – 5/22/22 – Norwich 0 – Tottenham 5

It had all come down to this. The culmination of a stretch run of four matches in fifteen days that would determine whether or not Spurs would be playing in the Champions League or the Europa League. A massive away draw at Liverpool, two home wins, and an Arsenal loss to Newcastle had pulled Tottenham just one point away from their first appearance in Europe’s top tournament since the 2019-20 season. All that stood in their way was a Norwich side who had yet again earned promotion in 2020-21 only to burn out and be relegated the very next season. While the season had come down to a single match, it was more than “just a match.” This was the culmination of a journey that began with the appointment of one Antonio Conte back on November 1st. It began with the banishment of ketchup, mayonnaise, “brown sauce, and fizzy drinks” from the team dining hall. It began with a commitment and a desire to return the North London club back to their heights. It would be quite a journey to reach this level, but as the season reached its final day of competition, Tottenham Hotspur Football Club needed just one more strong performance to write the desired ending to an incredible turnaround story. Thankfully, Spurs had more on their minds than just a single point.
The North London side piled on the pressure from the outset with the opening blow nearly coming in the seventh minute as Dejan Kulusevski found Pierre-Emile Hojbjerg in the box who squared himself with a simple touch but fired his shot just over the bar. The Danish midfielder nearly assisted Harry Kane in the 11th minute, but the England captain was denied at the door step by Tim Krul who made his first of eight saves on the afternoon. While the Dutch keeper made some really nice stops throughout the match, the quality of Spurs’ attack would shine bright and find its footing in the 16th minute. PEH would play a long ball onto mid-season signee Rodrigo Bentancur who cut into the box dragging two Norwich defenders with him before sliding a pass to wide open Dejan Kulusevski who just had to guide the ball into a wide open net to open the scoring for Tottenham. It would be the start of a big afternoon for the club. In the 32nd minute, Bentancur would force the hand of Norwich again as he stepped in the way of a pass from Tim Krul and picked out Harry Kane who found himself all alone seven yards from goal to double Spurs lead. While the lead was only 2-0 at the break, the North London side was in full control. That grip was further strengthened in the 64th minute when Kulusevski added a brace with an incredible curling effort that was destined for the back of the net (and for the number five spot on our list of top goals of the season) from the moment it left the foot of the Swedish international. With a win and the team accolades all but secure, it was time for the club to help one of their players accomplish a personal accolade.
Coming into the final matchday of the season, Tottenham forward Son Heung-min sat just one goal behind league leader Mo Salah in the race for the golden boot. While the South Korean made it clear in the build up his priority was securing Champions League, the rest of the squad desperately wanted Sonny to finish the year at the top of the goal scoring list. While the 70th minute minute started with a denial of Sonny alone on the break, it ended with a raucous celebration in front of the away supporters. After the initial attack was pushed out for a Tottenham throw-in, the club kept the foot on the gas to create an immediate second chance as Harry Kane would push the tempo with a pass to Lucas Moura just outside the 18-yard box and the Brazilian would show immense creativity with a spinning touch pass with his outside leg to free up Son for the goal. It was a beautiful move to find the South Korean sensation; a move that showed that the entire team wanted this accolade for the reigning Asian Footballer of the Year. All that was left was the cherry on top. That cherry would come just five minutes later when Lucas Moura’s free kick would find Son at the top of the box with a chance to cement his claim at the Golden Boot. Sonny would slip free of his man and fire a curling effort with his preferred right foot into the back of the net to put his team up 5-0 and ensure he would leave Loftus Road with his award as well as ensure he would land on the number four spot on out countdown of goals of the season. The last image of the day would be Son Heung-min hoisted high by Lucas Moura with his team around him celebrating in front of the traveling fans. It was the perfect way to cap off the improbable journey that was the 2021-22 season.
#3 – 1/19/22 – Leicester 2 – Tottenham 3

We now come to the match that was named the most improbable comeback of the season by the Premier League. While the finish at Leicester will be remembered by Spurs fans for a long time, the build up to this match seemed destined for Spurs to come away with a comfortable victory. Leicester would enter the match missing ten members of their team due to injury and international duty. While some clubs would have asked the league to move the match with fewer players missing, (*cough* ARSENAL *cough*) Leicester made it clear they would move on with the squad they had. Spurs would also be without a few key pieces as Eric Dier, Cristian Romero, and Son Heung-min would all be absent due to injury or illness. Even without these key pieces, the club from North London appeared to have the advantage on paper.
It was indeed Spurs who held the early statistical advantage as the quality chances definitely stacked up in their favor starting with a Harry Kane shot that just missed Oliver Skipp who would have tapped in his first career Premier League goal but was cleared off the line by a Leicester defender in the ninth minute. Kane saw another chance rattle off the crossbar in the 19th minute from a Harry Winks corner as it seemed Spurs were destined to collect the contest’s opening goal. After Lucas Moura’s chance was turned away for a corner in the 22nd minute, the match would be turned on its head when Leicester took the lead on a goal by Patson Daka in the 24th minute. The young starting XI for the Foxes had weathered the storm, and now it was on Tottenham to see if they were up for the challenge. The opening goal seemed to open up the Foxes’ attack as they nearly doubled their lead in the 34th minute as James Maddison forced Spurs’ captain Hugo Lloris into action with a terrific diving stop to keep the score at 1-0. This once again ignited the Tottenham attack as Pierre-Emile Hojbjerg nearly deposited a fumbled ball from Leicester keeper Kasper Schmeichel but his shot was heroically saved off the line by Marc Albrighton. The dam would finally break in the 38th minute as Skippy’s interception allowed Harry Winks to set forward Harry Kane down the right hand side who punished Caglar Soyuncu (who we will be sure to mention again this match) and leveled the match at one with the 250th goal of his club career. As the first half came to an end, the statistics and the scoreline did not paint the same picture. Spurs had out shot their opponent 14-5 in the opening 45 minutes and seemed to have been the better side. This would set up an incredible finish.
Antonio Conte’s men continued to dominate the match statistically in the second half but still found themselves level at one apiece. Japhet Tanganga’s 64th minute laser nearly put the team in front, but a strong Schmeichel save kept Leicester alive after a period of Tottenham superiority. Things were sent array again in the 76th minute as recent substitution Harvey Barnes played a sneaky reverse pass onto James Maddison whose shot, which appeared to be headed into the arms of Hugo Lloris, took a slight deflection off of Japh Tanganga and bounced over the French keeper, off the inside of the near post, and into the net for 2-1. According to Oracle’s stats, Spurs now had a measly 4.5% chance of winning this match and jumping ahead of Arsenal for 5th in the league table. There was still time, and hope was still there. Conte then looked to his bench for another attacking press subbing on Steven Bergwijn in the 79th in hopes of finding a goal. Hopes of that equalizing goal nearly evaporated in the final minute of normal time as a sliding tackle from the Danish Destroyer, Pierre-Emile Hojbjerg, prevented Harvey Barnes from icing the match for the home side. Oracle’s stats now indicated that Spurs now only held a 0.02% chance of winning, but to paraphrase Lloyd Christmas, there was still a chance for late drama. For a more indepth look at this late drama, please be sure to follow this link to “The Shove Seen ‘Round the World” by Podspur’s own Jeremy Morehouse. Jeremy wrote this piece in the wake of this match, and it is still a great snapshot of the moments that put this match into the number three spot on our countdown.
With the fourth official showing five minutes of added time, Spurs knew they would have to work quickly if they wanted to leave the King Power Stadium with anything to show from their work. The first plot twist came in what many thought were the dying seconds of stoppage time when Pierre-Emile Hojbjerg (a name who really stepped up on the evening) fired a nice cross into a cutting Matt Doherty who was able to chest the ball into his feet before being sent through the spin cycle by Caglar Soyuncu – told you he would show up again – allowing Steven Bergwijn to blast the equalizing goal into the back of the Leicester net with just five seconds of the added time remaining. While Tottenham fans around the world rejoiced at the tying goal, Stevie B and Harry Kane vehemently retrieved the ball in hopes that the 1.5% of winning Oracle’s stats now gave them would be enough to steal all three points. Leicester just hoped to get the ball deep into their attacking end and come away with the draw. This looked to be the case as Youri Tielemans, a midfielder who is applauded for his precision, looked to dump a pass beyond Hojbjerg, for the final moments. Hojbjerg intercepted the careless pass and gave way for one of the most unforgettable moments in Spurs’ incredible history of late match thrillers. Once again, I cannot put into words the moment, so let’s just enjoy this one together…
As celebrations broke out on the Tottenham sideline and in front of the visiting supporters, fans sat in disbelief. Not since that Champions League night in Amsterdam had we seen such late drama. As I spiked my phone in joy into the passenger seat in the parking lot of the Bowling Green, KY Sam’s Club, I could not believe my eyes as my phone read “GOAL! LEI 2 – TOT 3 Steven Bergwijn 90+7’.” Tottenham’s broadcast perfectly wrapped up this moment at the full time whistle: “they were going home with nothing, they leave with everything!” No wonder this goal found itself at the top of our Goals of the Season list. Thank you Steven Bergwijn for one of the most thrilling moments in Premier League history!
#2 – 2/19/22 – Manchester City 2 – Tottenham 3

It just occurred to me that this will make the fourth straight away matches on our countdown. Not a problem, just an observation. It is always a big deal though when Spurs are away to another one the “Big Six” clubs, especially league leaders and defending champions Manchester City. Entering the match, the chances of European football seemed bleak. The club had lost three straight Premier League matches and sat at eighth place in the table on just 36 points. Antonio Conte’s squad did have three matches in hand on West Ham and Manchester United, but time was of the essence if they wanted to reach those Champions League spots. A statement against the Citizens would go a long way to reach that goal of top four. Manchester City, on the other hand, seemed to be cruising to a fourth league title in five seasons, and could open up a 12 point gap on second place Liverpool with a win over the visitors from North London. The team in sky blue had also only dropped four points at home all season. All signs pointed to a Manchester City victory.
It was a quick start for Spurs as Ben Davies found Harry Kane just below the halfway line in the fourth minute as the England international turned to set his team forward on the counterattack. A quick pass down the left hand side set forward Son Heung-min (for about the 2374th time since the duo started playing together) who was all alone on Ederson as Ruben Dias and Joao Cancelo tried to chase down the lightning quick South Korean. In the process, Cancelo expected Sonny to cut onto his favored right foot and made a decision to commit to the challenge. The problem with that was he abandoned his man, Dejan Kulusevski. In his short time since his move from Juventus, the Sweden international had a handful of appearances for the club, and was selected for his first Premier League start. Son spotted Deki at the top of the 18-yard box, slid him a pass, and the Swede put his club out front 1-0 in the blink of an eye. It was the first of double digit goal involvements for the new signing, and it was the sign of things to come for the newly forged Tottenham front three. The rest of the first half would be dominated by the champions as they saw 67% of the possession and outshot Spurs 11-2 in the half. The good news for Antonio Conte’s men was that only one of City’s 11 first half shots were on target. The bad news was that one shot ended up in the back of their net. As Raheem Sterling’s long pass was spilled in and out of the hands of a diving Hugo Lloris, City captain Ilkay Gundogan was able to slide in the rebound to level the score in the 33rd minute. The half would end with that same scoreline after a flurry of Manchester City chances failed to test Lloris to end the interval. This would set up an exciting second half from the Etihad.
The second half possession was dominated by City (71-29), but Spurs were able to capitalize on their few chances, putting all four of their shots on target in the interval. Conte’s men once again took the lead in the 59th minute as Sonny took a pass from wingback Ryan Sessegnon and delivered a pinpoint pass to a streaking Harry Kane whose right footed flick slipped past a rooted Ederson and into the top right corner for 2-1. It appeared that Harry Kane gave his team a 3-1 advantage in the 73rd minute but VAR deemed that Dejan Kulusevski was JUST offside in the build up to the goal. The match took a cruel turn in the 90th minute when another VAR check deemed that a sliding Cristian Romero had indeed played the ball in the box with his hand to set up a Manchester City penalty. Riyad Mahrez would equalize the match on the ensuing penalty in the second minute of stoppage time. As he celebrated the NBC Sports commentators roared with “City have stoppage time to win it now!” I am not as critical as NBC’s bias towards Manchester City as other fans, but that is incredibly egregious for an “unbiased” broadcast company to say on air in a big match. It would have been a shame if someone in lilywhite made him eat those words…
As the match entered the fifth of seven minutes of stoppage time, Spurs were on the attack once again as Rodrigo Bentancur sprung Kulusevski down his right flank and into the depth of the City end. Deki gathered the ball and cut back towards the box as multiple teammates crashed the net looking for a cross from the Swede’s favored left foot. His cross would rise too high for the head of Lucas Moura, but former Tottenham right back Kyle Walker failed to attack the cross with any conviction allowing Harry Kane to smash in the winner on the evening. As Kane sprinted away in celebration, I can only reflect on the Harry Kane summer drama. From forcing myself to realize the Kane-era at Tottenham was over, to the he-said-she-said as reports came in about City’s formal bid that never came, to the appointment of Nuno Espirito Santos that seemed to further submit that Harry Kane’s desires at the club were dead. Then, a jolt from Antonio Conte finally allowed us to see shades of the real Harry Kane: the reigning golden boot winner and playmaker of the year in the Premier League who is the best pure striker in the world today (and there is no argument about that)! This moment signalized to me that the entire team was all-in for Conte-ball. Now they just had to finish the job.
And now, for the moment you have all been waiting for…
#1 – 5/12/22 – Tottenham 3 – Arsenal 0

As the month of September came to a close with a resounding Arsenal win over our beloved Spurs, I was hopeful for revenge in the reverse fixture at Tottenham Hotspur Stadium in mid-January. As the match drew nearer, that sense of excitement and nerves started to fill my stomach even after Chelsea had knocked Spurs out of the Carabao Cup semifinals. Spurs were finally adapting to Antonio Conte’s system after two months in charge, and Arsenal was going through growing pains as their young roster adapted to the Premier League. Then, the unthinkable happened. Arsenal was to be without a few players due to injury and international duty, so instead of calling up some of their academy players or recalling players on loan to fill their squad as the likes of Leeds United and Leicester City had been forced to do, they successfully petitioned the league to postpone the match. They got scared and they ran. I had just hoped Spurs would have the last laugh in the situation. This is the set up for the top match of the 2021-22 season!
As they smoke cleared entering the final midweek match of the season, Arsenal sat four points in front of fifth-place Tottenham Hotspur with just three matches to go on the season. Spurs knew a loss would end their hopes of Champions League and bring back some ancient holiday that I will not mention because, in my time of supporting the club, it has never existed. A win on the other hand would put the pride of North London just one point behind their fiercest rival with just two matches to go. It was for sure to be an instant classic North London Derby filled with intrigue and unforgettable moments.
The match started with Arsenal on the front foot collecting a couple of early chances, but a small scuffle in the 12th minute between Son Heung-min and Ben Holding would set in motion the narrative that would hang over the entirety of this match. In the 21st minute Sonny was fouled as he was sandwiched by Rob Holding and Cedric Soares at the back post as he tried to reach a Dejan Kulusevski cross. It was now up the all-time leading goal scorer in the history of this derby to put the home team ahead. Kane would be up to the task as he was able to force his England teammate Aaron Ramsdale the opposite way of his clinical penalty to put Spurs ahead 1-0 in the 22nd minute. The crowd was deafening in response to the opener as the new home of Tottenham Hotspur was finally able to host a North London Derby with full attendance. That support and noise did not let up for the entire match. The roar would crescendo once again when Son and Rob Holding were tangled again leading to a yellow card for the Arsenal defender in the 26th minute, but it would not be the final time these two would combine to impact the match. That moment came just six short minutes later as Sonny’s attempted run behind Holding was deterred by the defender’s forearm shiver that forced the defender off with a second yellow card. Spurs now had the numerical and the fan advantage, it was now up to them to ride the momentum to victory. Conte’s men would strike just a few moments later as a corner kick was directed towards goal by the head of Rodrigo Bentancur and knocked over the line by a diving effort from Harry Kane. The stadium erupted at the sight of the English captain’s diving effort as they knew their hopes of seeing Champions League football were very much alive. It was the cap to a stellar first half performance that saw the home team control almost every statistical category. Now all that was needed was to go to Home Depot for a little bit of finish.
The second half would see Spurs return with said finish as they used their man advantage to dominate possession, shots, passing, and dangerous attacks. The perfect ending to this incisive Tottenham victory came just two minutes into the second half as Davinson Sanchez, who was a surprise addition to the starting XI after Cristian Romero was forced out of action with a hip injury, found Harry Kane posted up inside the box. Kane was unable to create separation from his defender, but as he fell to the ground making a turn, the ball bounced to a coiled Son Heung-min who made no mistake and blasted home his attempt for 3-0. It was a fitting end to the scoring as the South Korean moved just one goal behind Mo Salah in the race for the golden boot. With their marquee men leading the way, Spurs would see off the rest of the match and move just a single point behind the Gunner in the race for 4th place and a spot in next season’s Champions League. In my six seasons supporting this club, this match felt bigger than any other Premier League match that I had experienced. Even with Arsenal holding their one point lead in the league table, it felt like Spurs had broken their spirit and asserted themselves as a Champions League side. All these things lead to this match being the top match of the 2021-22 season.

There you have it, my list of the top ten matches of the season. Did I get it right? Am I missing one? Please feel free to comment on this page or let me know on social media of your thoughts. Be sure to join us next Tuesday and Thursday as I bring to you my top ten moments of the season. What individual achievements made the cut? What new arrival had the greatest impact on the season? I will answer all of those questions next week here on the Podspur blog.
Thanks for reading. If you’d like to follow me on Twitter, you can do so by clicking here. Let me know your thoughts in the comments. COME ON YOU SPURS!
-Dustin Gentile