The 2023/24 season began on the 13th of August 2023 for Tottenham Hotspur when they travelled to Brentford and finished with a visit to Sheffield United. This marked the completion of a rollercoaster decade of seasons since the appointment of Mauricio Pochettino as manager of the club.
In this time, we have seen Spurs compete in all three of UEFA’s club competitions, a couple of title pushes, a Champions League final appearance and seven different managers appointed, including the ones on an interim basis.
We are about to embark on an attempt to rank these last 10 seasons from worst to best. Of course, without any trophies to take into consideration when trying to sort through these seasons, let’s use moments, circumstances and performances to differentiate the good from the bad with this list.
(10) 2022/23
Some may call it recency bias, others will just call it a disaster, you couldn’t say the 2022/23 season wasn’t eventful. A very optimistic, somewhat sad in hindsight, excitement grew in the build-up to this season. Antonio Conte had his first pre-season with the club and Spurs made some interesting signings that looked to shape a more Conte-appropriate squad. The three most notable names that were brought in were Ivan Perisic, Richarlison and Yves Bissouma for a combined £74 million (transfermrkt).
There were a few bright moments in this season. Spurs’ 4-1 opening day win over Southampton as well as a battling performance during a visit to Stamford Bridge gave everyone a tragic false sense of hope, while Harry Kane’s goal to beat Manchester City in February crowned him the club’s all-time greatest goal scorer.
But as the months of the 2022/23 season rolled on, the results became very poor. Some examples of this include the 3-3 draw at Saint Mary’s which led to that infamous Conte press conference, the demolition by Newcastle at St James’ Park, and the comeback that never was at Anfield.
By the end of the season, it seemed the club was in a very dark place. Three different people in Conte, Cristian Stellini and Ryan Mason had taken charge of the Spurs team by the time the season ended. Spurs had finished without European football for the first time since the 2009/10 campaign (The Athletic) and a sour taste was left in the mouths of everyone involved both inside and outside of the club. By far the worst campaign on this list.
(9) 2020/21
One word to describe this one? Strange. The world wasn’t anywhere near out of the shadows of Covid, and fans were still locked out of stadiums. Jose Mourinho was preparing to take on his first full season at Tottenham Hotspur and brought Pierre Emile Hojberg, Sergio Reguillon and Matt Doherty into his ranks, but the most intriguing move of them all came in the form of the long-awaited return of Gareth Bale (transfermarkt).
Mourinho saw a bright start to the season for his side, Kane and Son forming a deadly partnership during Spurs’ run of only one loss in their opening 11 Premier League games (Sky Sports). Spurs’ run of form in the first half of the season was complimented by topping their Europa League group, a League Cup run and a bizarre visit to Marine when they entered the FA Cup.
But results would begin to falter, and inconsistency became prevalent as the season progressed. Spurs were knocked out of the Europa League in the last 16 having lost a 2-0 lead that they brought to Dinamo Zagreb. They had already dropped out of the FA Cup after a frenzy at Goodison Park which saw them beaten in extra-time by Carlo Ancelotti’s Everton. Spurs did have a League Cup final to look forward to, but not under Mourinho with his spell in North London ended just days before.
This tough period for the club also coincided with the announcement and subsequent disbanding of the controversial European Super League which left many fans sickened at the club. Spurs would finish out the season with Ryan Mason at the helm, finishing 7th, making them the first English club to qualify for the UEFA Europa Conference League.
(8) 2019/20
We’re nearing closer to the better times, but first let’s reminisce about the 2019/20 season. Of course, you could do this by logging onto Amazon Prime. Fresh off the back of a Champions League final hangover, the higher-ups at Tottenham put their hands in their pockets and splashed out to sign Tanguy Ndombele for a club record £52million (transfermarkt). It was Spurs’ first full season in their brand-new stadium, filled with hopes that Spurs could push on again after the disappointing loss to Liverpool in Madrid.
Tottenham’s league form didn’t leave much to be desired in the latter stages of the previous season, which we’ll get on to later, and unfortunately, this poor run followed them into the new campaign. Three wins in their first 12 league games (Sky Sports), paired with a League Cup defeat to Colchester, ended Mauricio Pochettino’s five-year stint at Tottenham Hotspur. This was followed by the shock appointment of Jose Mourinho as manager, the beginning of a new era at the club.
Mourinho did well in his attempt to steady the ship at Spurs and saw a slight upturn in form. Spurs would also get out of their Champions League group only to be beaten by RB Leipzig in the last 16. The Covid-19 outbreak saw the Premier League, and indeed the whole world, be put on pause and Spurs wouldn’t play another game until June. Only one loss in the nine games after the restart saw Spurs finish 6th, a respectable result all things considered.
(7) 2014/15
From Poch’s last season, to his first at the club. Spurs brought in the Argentine as their head coach from Southampton in the Summer of 2014 after an impressive stint with the Saints. The transfers are the most fascinating part of this season as they quite simply laid the groundwork for Pochettino’s tenure at the club, bringing in the likes of Ben Davies, Eric Dier and Dele Alli (transfermarkt).
While not many moments of note Pochettino proved his worth, a steady season Spurs finishing 5th in the league and being defeated by eventual league champions Chelsea in the League Cup final. The most important aspect of this season and the reason it is given this spot on the list is the emergence of a young Harry Kane. Kane burst into the squad from the academy to the excitement of many fans and made sure he was there to stay.
Kane would finish the club’s top goalscorer with 21 goals (transfermarkt) and many wondered what the future held for Pochettino and the squad of young talent he was beginning to build at White Hart Lane.
(6) 2023/24
Need I delve too much into this one? Tottenham turned to Celtic’s Ange Postecoglou to bring his fresh attacking football to North London and to pick up the pieces of the club which had been torn to shreds over the last few years. And overall, I believe Postecoglou has begun to do that with Tottenham after his first season in charge.
Spurs finished 5th this season, having to deal with multiple injuries and mid-season continental tournaments along the way. The reason it pips 2014/15 to this 6th place spot is purely down to the fact that we don’t know what is around the corner and a level of excitement has built around the club once again.
(5) 2021/2022
If you want a definition of “rollercoaster” in terms of Tottenham Hotspur, you can point to this season. In the wake of the Mourinho mess, Spurs appointed his compatriot Nuno Espirito Santo as his successor, fresh off the back of an impressive few years at Wolves. Notable additions from this summer include Cristian Romero, Emerson Royal and Bryan Gil (transfermarkt). The club also had to spend the summer batting off rumours that Harry Kane was set to leave Spurs to join the blue side of Manchester.
This was what made a victory over City on the opening day all the sweeter for Spurs fans, Son scoring while Kane watched on after a lengthy Euros campaign. This match, along with the two other 1-0 league wins that followed it was probably the highlight of Nuno’s tenure as Spurs would go on to lose the next three games after them (Sky Sports). Spurs’ involvement in the inaugural season of the Europa Conference League didn’t get off to the most convincing start either, and after 17 games with just nine wins, Nuno was sacked in November.
Enter Antonio Conte, the Italian brought in with the hopes he’d bring his winning mentality to the club with him. Conte’s appointment saw an uptake in league form, managing to be unbeaten until a 2-0 defeat to Chelsea near the end of January. Spurs crashed out of the Conference League in the group stages after a Covid outbreak within the squad meant they couldn’t play their final game; their opponents Rennes being awarded the victory as a result. Spurs’ strong finish to the season could be credited to two January signings in the forms of Rodrigo Bentancur and Dejan Kulusevski from Juventus.
Bentancur brought a certain stability and class to Conte’s midfield, while Kulusevski lit up Spurs’ right-hand side when he arrived in January, bagging 13 goals and assists in the second half of the season. The months rolled on and it was clear Conte shook off Spurs’ mediocre start, they were making a push for Champions League football.
This culminated in the famous head-to-head when Arsenal visited in May, the winners taking pole position in Champions League qualification. Spurs bullied Arsenal to a 3-0 victory that night and won their last two games of the season to finish 4th. Spurs seemed to be in a good place, with a world-class manager and Champions League football to go with him. Not many could have foreseen what happened after that.
(4) 2017/18
The Wembley years. We’ve come to the part in the list that is mostly enjoyable to look back on. White Hart Lane had undergone demolition and Pochettino had Spurs cemented as one of the big players in the Premier League. This season’s transfers will fill you with nostalgia with Davinson Sanchez, Lucas Moura, Serge Aurier, Fernando Llorente, Juan Foyth and Paulo Gazzaniga all entering the fold (transfermarkt).
Spurs’ league form was impressive in this campaign, only losing seven games and amassing 77 points, finishing third yet nowhere near champions Man City who grabbed 100 points in a famous season for the Blues (Sky Sports). Spurs’ Champions League run was interesting to say the least.
They were drawn in somewhat of a group of death alongside Real Madrid, Borussia Dortmund and APOEL but managed to stay unbeaten and top the group. Pochettino led Spurs to an impressive win against the reigning and eventual European champions Real Madrid at Wembley. This run wouldn’t last very long though as Tottenham would be knocked out by Juventus in the Last 16.
This season was one which the fans had come to expect from Pochettino and his squad. Spurs even made it to the FA Cup semi-final where Dele Alli did a Fortnite dance before they were defeated by Manchester United in their temporary home.
(3) 2015/16
The one that kickstarted it all for Pochettino and Spurs. A year under his belt, and an opportunity to mould his squad in the way he wanted it, Pochettino was ready to take on the league with a young team. A summer transfer window that would have a huge impact on the club over the following few years saw names like Heung-min Son, Toby Alderweireld and Kieren Trippier join the club for a combined £44million (transfermarkt).
Spurs’ league season started brightly, only losing twice before Christmas (Sky Sports), and Harry Kane was proving he was much more than a one-season wonder. But Tottenham had a big blue force of nature blocking their way, Leicester City. Leicester, who barely managed to remain in the Premier League in the previous season, appointed Claudio Ranieri as manager in the summer and began a fairytale run at the league summit. Pochettino’s first chance at league glory was being halted by a club who were playing in the championship a couple of years beforehand.
As the season ran into its final weeks, a weariness began to show within the squad. Spurs could only win four of their last 10 games, drawing four times and losing twice (Sky Sports), while it looked increasingly likely that Leicester would do the impossible. Tottenham were still in the title come the third last game of the season when they travelled to Stamford Bridge.
A fiery game ensued dubbed “The Battle of the Bridge”, where a struggling Chelsea came from two goals down to level the game and hand the title to Leicester. Spurs committed 20 fouls that night and received nine yellow cards (Premier League), many in the media claiming they self-destructed.
(2) 2016/17
Fresh off the back of a title challenge in the previous season, Spurs were looking dangerous. Pochettino added Moussa Sissoko and Victor Wanyama to his midfield ranks (transfermarkt) and looked to push on after his side’s breakthrough season in the last campaign. This was a monster side. It was Spurs’ last season at White Hart Lane, and they weren’t leaving it without entertainment.
It could be argued that Spurs were unlucky to be once again vying for a title against a team that seemed to be steamrolling towards it. Our old pal Antonio Conte had cracked the code at Chelsea after a few challenging opening months at Stamford Bridge and they didn’t falter on their way to the top after he did. Tottenham only lost four league games this season, twice in 2016 and twice in 2017, but not one of these losses came at the Lane in its final season (Sky Sports).
Tottenham finished the season seven points behind Chelsea, but with the best attacking and defensive records in the league (fbref.com). They paired their impressive domestic form with a run to the FA Cup semi-finals where they would also lose out to Chelsea.
The only fault to this season, despite not winning any trophy of course, was Spurs’ bizarre European run. Their flying form in the league did not translate into their European ties, finishing third in a Champions League group that featured the famous Monaco side that held Kylian Mbappe, Thomas Lemarr, Bernardo Silva, Radamel Falcao, and Fabinho, along with Bayer Leverkusen and CSKA Moscow. Their demotion to the Europa League didn’t last long either, losing to Gent in the round of 32.
(1) 2018/19
Could this be a controversial number-one pick? Maybe. Pochettino’s Spurs looked like they were slowing down slightly, after arguably being the club’s most impressive sides in its more recent history, they didn’t have any silverware to show for it. This wasn’t aided by the fact that the club failed to make a single signing during this season, something that frustrated the fans and Pochettino. This became evident on the pitch, Tottenham losing over 10 league games for the first time in years.
Despite only winning three of their last 12 league games, Tottenham would hang on to a Champions League spot by a single point (Sky Sports). They were knocked out early in the FA Cup by Crystal Palace and were gotten the better of once again by Chelsea in the League Cup semi-finals. So, what gives this season the number-one place on this list? The Champions League run of course. Much the opposite to the 2016/17 season, this time Spurs’ poor domestic form translated into electric European form.
Spurs finished second in a group containing Barcelona, Inter Milan and PSV, and things only got more intriguing in the knockout rounds. Spurs breezed past Dortmund in the last 16, then were saved by VAR to knock out Man City at the Etihad in the quarterfinals. Then came the famous night in Amsterdam where it looked like Tottenham’s race was run, until a magical second-half hattrick from Lucas Moura brought Spurs back from the brink to book a place in the final in Madrid. Spurs would of course be pipped at the final hurdle by Liverpool, who were having an electric European run themselves and Tottenham’s dreams of a first Champions League title were finished.
Yes, they didn’t win it, and their league form wasn’t anything to write home about but the memories of going back and forth with Barcelona at Wembley, Pep Guardiola falling to his knees when Raheem Sterling’s winner was chalked off by VAR, and Lucas rolling a third goal past Onana in the dying seconds away to Ajax will forever live on. And we all know what proceeded this, so it’s nice to remember the happy times.
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