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.
Here are the countdowns from the previous weeks:
Week 1 – Goals of the Season – Part 1 – Part 2
Week 2 – Matches of the Season – Part 1 – Part 2
Without much further ado, let’s look at this week’s list…
Moments of the Season (#10-6)
When looking at the top moments, there are a few standout candidates for the best of the season. When compiling this list the criteria was simple, what moments had the greatest impact on the season. From the highest of highs to the lowest of lows, I will be bringing you the moments that made 2021-22 the roller coaster it was. Typically, I start off with a few honorable mentions, but this week, we are going to jump straight into our list.
#10 – Nuno Espirito Santo wins manager of the month

When Nuno Espirito Santo was named the newest manager of Tottenham Hotspur Football Club, the appointment brought an end to one of the strangest managerial searches in the history of the sport. Time and time again, the club thought they had a manager for a report to come out just days later that the manager had declined the offer for whatever reason. It was a never ending saga that seemed destined to loom large over the remainder of the summer. Even when the former Wolves manager was appointed, many fans saw this as a temporary fix (hold onto that thought). Then things started to seem even more bleak when star striker Harry Kane started his own saga as he made it known he wanted a new challenge. While that challenge never came to fruition there was still little hope for the Nuno era, especially when his first official match in charge saw Spurs take on the defending champions.
Then, something unexpected happened. Manchester City left Tottenham Hotspur stadium on the wrong end of a 1-0 loss. Sure the Citizens saw the vast majority of the possession and peppered the Tottenham defense with a relentless attack all afternoon, but when the dust settled, it was Nuno who had led his team to a 1-0 victory. A win is never a bad thing if you are a Premier League manager (hold on to that thought as well). Next up in the Premier League was an away matchup to Wolves. The same Wolves team that Nuno had just left after he guided them from the Championship to the Premier League, and even into the Europa League in three consecutive seasons. A Dele Alli penalty was all the visitors needed to come away with their second consecutive 1-0 victory under their new manager. His style was not the high flying system Spurs fans had fallen in love with under Maricio Pochettino, but the ultimate results were there. A win in matchweek three would see Nuno take his Spurs to the top of the Premier League table, which is a sentence no one thought they would utter during this season. As Spurs hosted newly promoted Watford, it would take another 1-0 effort to vanquish the visiting Hornets and see the squad sit atop the Premier League table headed into the first international break of the season. Three matches, three wins, three goals. That is all it took.
It had been an unpredictable start to the Nuno era. No one expected his team to top the league in spite of all of the drama surrounding the club. No one expected the club to knock off the champions on the opening day of the season. No one expected three consecutive 1-0 victories would get the job done, but Nuno had defied all of those expectations. It was now time for the Portuguese manager to defy one more expectation. That would occur on September 3rd as Nuno Espirito Santo would be named Premier League Manager of the Month! Maybe it was time to trust the manager who promised to “make [us] proud.” More to come …
#9 – The January departures of Ndombele, Lo Celso, and Dele

The day was January 31, 2022. The final day before the closing of the January transfer window. So far, Spurs had sent the following players out on loan: Kion Etete, Jack Clarke, and Nile John. For a team looking to freshen up a squad that had been crying out for a “painful rebuild,” three youth players was not the idea most fans had for this shake-up. Then, a trio of dominos started to fall that would spark signs that Spurs were looking to start fresh.
The first domino that fell was a loan move for record signing Tanguy Ndombele back to Ligue 1’s Lyon. The tenure of Tanguy Ndombele in North London could be best summed up with a single question, “what if?” What if the French international had hit the ground running after a good showing in Singapore at the International Championships Cup where he assisted Harry Kane with just his second touch in a Spurs shirt and he scored an equalizing goal in the Premier League opener against Aston Villa that would spark a Tottenham turnaround? What if he would have been able to get his fitness up to a level where he was reliable on both the attack and the defense prior to the sacking of Mauricio Pochettino? What if we would have gotten consistent play from the Frenchman that rivaled his performances against Manchester City in the Champions League while playing for Lyon? What if four managers in three seasons was more detrimental to the midfielder than we could understand? I could continue to play the what if game, but I think we all get the point. The biggest thing that plagued the record signee from day one was his output. Here are the raw numbers. The £63 million signee appeared in 89 matches making 63 starts. In those appearances, he tallied nine goals and nine assists while accumulating an average match rating of 6.86 out of 10. While those numbers do not seem bad, the most telling statistic is that Ndombele played 4935 minutes in those 89 matches, for an average appearance of … drum roll please … 55.4 minutes per appearance. For a record signing, that statistic should be a huge red flag. The other statistical red flag that appeared to me was the fact that he averaged one goal involvement every 274 minutes. At 55.4 minutes per appearances, our record signing, who was brought in to help progress the ball through the midfield and be a new creative outlet, was averaging a goal involvement once every five matches. It was more than the statistical output thought. Match after match, we saw this man lumber around the pitch and consistently offer nothing in terms of a defensive output. Many fans saw his eventual return to Lyon via loan as an addition by subtraction.
Our next move on deadline day would see another 2019-20 signing go out on loan. Central midfielder Giovani Lo Celso was officially sent out on loan for Villarreal shortly after the announcement of the loan move for Tanguy Ndombele. The £42.3 million signing seemed to divide opinion among Spurs fans as he showed flashes of promise, but for a man who was believed to be the replacement for Christian Eriksen, it just never seemed to come together for the Argentinian. He also suffered from another what if scenario. In the summer of 2019, Spurs chose to sign GLC as their understudy to Eriksen over another young talent who would find his way to the Premier League in January of 2020. Lo Celso would make 79 appearances for Spurs and total six goals and six assists while battling injuries early in his time in North London and struggling to crack the lineup under both Jose Mourinho and Antonio Conte. What about that other young talent? Well in all competitions since his move to England, he has made 126 appearances tallying 50 goals and 40 assists… Choosing Giovani Lo Celso over Bruno Fernandes was definitely a missed step for the club. While his time with Spurs has not been as near as frustrating as Ndombele’s, his January exit definitely signaled that the painful rebuild was in full swing.
Speaking of painful rebuild, the last exit of the January moves might have been the most necessary while simultaneously being the hardest good-bye of them all. In a move that signaled the painful rebuild was definitely in full swing, it was announced that Everton had secured the permanent move for 2015-16 and 2016-17 PFA Young Player of the Year, Dele Alli. It was a tough pill to swallow for many of us fans. The £5 million transfer from League One’s MK Dons made an instant impact when he arrived at the start of the 2015-16 season. The England international would go on to make 266 appearances for the club netting 66 goals and 56 assists. He was an integral part of two title charges and the club’s unprecedented run to the 2019 Champions League final. So… what happened over the last two and a half seasons? Some argue that the club should have sold Dele at the end of the 2017-18 season when his value reached his peak at £90 million. Even after the end of the 2018-19 season, the midfielder’s value still hung at £80.7 million. Maybe the transition to Jose Mourinho was not what Dele needed. Some will point to the fact that Dele’s form took a major dip when Christian Eriksen was sold, which inhibited his ability to roam creatively? Whatever the reason, it was painfully obvious that Dele needed to go as he clearly was not a part of the vision for Antonio Conte’s Tottenham Hotspur. It was sad to see him go, but the departure of Dele Alli sealed the deal on the notion that Spurs were moving forward. It pains me to say that losing Dele was addition by subtraction as he provided many moments early in my time supporting the club that I will never forget, but you could tell he was done. His body language, his on field performance, his whole being cried out for a change of scenery. The departures of these three players set the tone for what was to come in the final months of the 2021-22 season.
#8 – Return of the Kane – Harry Kane bosses the Etihad to lead Spurs to victory

Over the past two weeks, I have teased giving everyone my take on the Harry Kane summer transfer that failed to materialize. Well I think it is time we talk about it. According to the striker, he and Tottenham chairman Daniel Levy had a gentlemen’s agreement to let Kane leave during the summer of 2021. Kane expressed a desire for a new challenge and it seemed that he was destined for a nine-figure transfer to defending Premier League Champions Manchester City. Kane had hoped this deal would be completed before he left for the rescheduled Euro 2020 event. Well, that did not happen. This seemed to negatively impact the striker as he struggled through the opening matches of the competition. As the tournament drew to a close, the England captain would see a huge uptick in form, scoring four goals in the knockout round and leading his squad to the tournament final, England’s first major final since 1966. While the Three Lions would fall in penalties in the final, it seemed as just a matter of time before Kane would don a sky blue kit and play for Pep Guardiola. Reports say that the champions tabled multiple offers with Spurs with the largest offer climbing as high as £125 million. This was still insufficient in the eyes of Daniel Levy who demanded £150 million for the striker’s services on the low end.
Then the saga became a lot more convoluted. After his performance at Euro 2020, a report came out that Harry Kane would miss the beginning of Spurs’ preseason training so he could take a vacation. Not that his recent performances did not warrant him enjoy some time away with his family, but the report came out of nowhere. Then to add to the rumor, it was reported that this was agreed upon prior to the start of Euro 2020 by Daniel Levy. Levy and the club denied this agreement as more rumors swirled that Kane was holding out to training. Confused? I am, too. Kane would comment on those rumors a few weeks after the Euro saying, “while I won’t go into the specifics of the situation, I want to clarify that I would never, and have never, refused to train.” So as the summer ended and Kane missed Spurs’ pre-season friendlies, many wondered if Spurs fans would get to see Harry Kane in the season opener against Manchester City … in the sky blue of the Citizens. That thought ended as it came out that he would be unavailable for the season opener. When Kane did return to the field, his performances were disjointed. He seemed uninterested in Nuno’s system and did not look like the reigning Premier League Golden Boot winner and Playmaker of the Year.
Then, things started to change. As the Nuno era unceremoniously ended after a 3-0 home defeat to Manchester United, the hiring of Antonio Conte seemed to breathe new life into the England captain. We saw him play with that spark. He started to score the types of goals that made him the club’s all-time leading Premier League scorer. He started to drop deep and pick out his teammates with the quality and precision he had the year before. Long story short, we saw the return of the old Harry Kane, which is what brought us to that February night at the Etihad. Six months prior, I was convinced that Harry Kane would be playing for City on this night, and we would have (hopefully) turned his record fee into some needed new talent; however, I am happy to say that was not the case. The Harry Kane we saw that night put in the best single performance any player in a Tottenham shirt had ever put up against Manchester City. He completely dominated the Etihad with one of his all-time performances. It felt like for the first time all season, we had seen a fully invested Harry Kane who acted like he had something to prove. That night showed the whole world that Antonio Conte’s Spurs could make a very large impact on the fabric of the Premier League.
#7 – Kane and Son break the record for most goal combinations in PL history

From the perspective of an outsider, Son Heung-min’s 85th minute goal to put visiting Tottenham Hotspur up 4-0 on Leeds may not have seemed like a big deal. I mean, the visitors ambushed a Leeds team who fought to avoid relegation for most of the calendar year 2022 in the first half with three impressive goals to open up a commanding lead on the afternoon. Then they decided to play add on as the match was rapidly approaching its end. It would have been easy for the casual fan to pay no attention to this goal, but those who know the game, this goal was one of historic proportions.
While the partnership between Son Heung-min and Harry Kane had been respected since the pair consistently connected for goals in the 2016-17 season, one performances in the early stages of the 2020 season really put the league on notice that they were an all-time combination. On that September 20th afternoon, Harry Kane would find his strike partner, Son Heung-min, four times in one match. You read that right, FOUR times. It would be the start of a magical season where the duo would connect for 14 goal combinations in one season, which set the single season Premier League record. It also put them in contention to catch Didier Drogba and Frank Lampard for the most goal combinations in league history. It would set the stage for that February afternoon where the two would etch their names into the Premier League record books.
The goal was textbook Kane and Son show. Harry Kane had just received a short pass from Pierre-Emile Hojbjerg and managed to create a little time and space as he approached the halfway line. He then spotted the darting run of the South Korean and served up a picture perfect pass. Sonny was able to chest the ball down to his feet at the top of the 18-yard box with his first touch and put the ball into the back of the Leeds net with his second. The celebration was the perfect sign of the connection between the duo as Sonny raced back up the pitch before sliding into a big hug from his teammate. The moment was perfectly called by Rob Daly on Spurs TV, “Kane and Son, Spurs legends. Now a record breaking duo. That was a perfect representation of what these two are all about.” The moment can be best summed up as the duo turn to the visiting supporters and they simultaneously point at each other.
As someone who only started supporting this club since the 2016-17, Son Heung-min and Harry Kane have been my two favorites from the outset. Sonny was actually the player that cemented me as a Spurs fans with a stellar performance at Middlesbrough, and it was virtually impossible for me to not be a Harry Kane fan during his incredible 16-17 season. Since that time, the group always seemed to not get the credit they deserved. While I still feel like they do not get the respect they deserve (I will come onto that with next week’s countdown), this accolade is something that you can never take from them. I know records are meant to be broken, but with this goal in those (forgive me) ugly gumball kits cemented the fact that you could not talk about the greatest goal scoring duos in Premier League history without mentioning Son Heung-min and Harry Kane.
#6 – Nuno Espirito Santo is sacked as manager of THFC

Sir Issac Newton’s third law of motion states that for every action force, there is an equal and opposite reaction force. Well. remember how we started this week’s list with Nuno Espirito Santo’s award winning start to his time at Tottenham Hotspur? That unfortunately was the action force. The equal and opposite reaction force would come in the way of the manager’s sacking on Halloween of 2021. The Nuno era might have started with Spurs reaching the pinnacle of the Premier League, but most everyone knew those results were not sustainable. We have mentioned at length the Harry Kane transfer saga, so will not revisit that issue. There was also that horrific performance at Portuguese side Pacos de Ferreira that saw the club dig themselves a 1-0 hole in the qualifying round of the UEFA Europa Conference League. Then there were the Derby Day debacles at Crystal Palace, Arsenal, and Chelsea with a lack luster draw in the opening match of the group phase of the Conference League. While the club did rattle off three straight wins in October, the end of the month would spell the end of a very quick era. A Conference League loss to Vitesse was followed by another derby loss to West Ham and a lackluster win at Burnley in the Carabao Cup. This paved the way for the final nail in the coffin.
Entering Spurs’ October 30th match against Manchester United, the match made all the headlines for all the wrong reasons. While Spurs were struggling to gain any consistency during the Nuno era, Manchester United was also dealing with a coach who was also on the hot seat. Ole Gunnar Solskjær had made a tremendous start when he took over for Jose Mourinho in 2018, but his recent performances had seen many fans turn on the former United player. The poor form from both teams had lead to the matchup being dubbed “El Sackico” by the media. Lose this match, and lose your manager. It was the background for the number six moment on our list. A lackluster first half was capped by Cristiano Ronaldo’s 39th minute opener to give the visitors a 1-0 halftime lead. The second half began with the same lack of intrigue the fans saw in the first half, and Nuno responded by going to his bench in the 54th minute. It was at that moment, fans saw the live end to the Nuno Espirito Santo era as he elected to sub on Steven Bergwijn for Lucas Moura. This was not the substitution the fans were crying out for, and their disdain was very clearly heard. Manchester United would respond with a goal from Edinson Cavani before capping off the match in the 86th minute with a strike from Marcus Rashford. With a 3-0 victory, Manchester United had officially won “El Sackico” (well … just hold on to that idea for now), and Spurs would bring an end to the Nuno era in North London the following day.
When the dust settled on his time as manager of Tottenham Hotspur Football Club, Nuno’s teams won eight times, drew twice, and lost seven matches. In those 17 matches, Spurs scored a total of 22 times while allowing 23 goals of their own. Those numbers definitely spelled the end for the former Wolves manager. All in all, I think my friend and fellow Spurs supporter, Jacob Gaddie, perfectly summed up the relationship between Nuno and the club: Nuno was like that girl you date for a short period of time after your heart is broken by your longtime girlfriend. She is there to help you rebound, but the relationship is not going to amount to much more than that. Then, you move on to a more serious relationship. We will definitely get to that more serious relationship very soon.

This brings us to the end of part one. Be sure to check back in on Thursday as I unveil my top five moments of the 2021-22 season, which promises to be full of late drama, derby day performances, and fresh new faces in North London.
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