In January 2019, Mauricio Pochettino clarified his stance on what defines success for Tottenham Hotspur.
Three days after losing against Chelsea on penalties in the semi-final of the Carabao Cup, his side were eliminated by Crystal Palace in the FA Cup fourth round. It was the second time in four years the south Londoners had knocked Spurs out of that tournament, leaving their chances of winning a trophy that season hanging by a golden Champions League thread, with Manchester City and Liverpool running away from the pack in the Premier League.
“We are going to create a debate that to win a trophy is going to help the club,” Pochettino said in a post-match press conference after that Palace defeat. “I don’t agree with that. That only builds your ego.
“In reality, the most important thing is being consistently in the top four and playing Champions League. That is going to help the club to achieve the last step. Today, the club is doing fantastically, it’s so successful. In the last four or five years, we’ve been fighting in different ways to achieve what the club needs, to be in the level of Chelsea, United, City or Arsenal or Liverpool.”
Without the same financial clout as some of his rival managers, Pochettino may have had to prioritise one or the other. After all, while his team competed in vain towards the top of the Premier League table without adding another trophy to the cabinet, the club also built the most impressive football stadium in the country.
Rarely is the qualification for the Champions League six times in the drought period referenced by neutrals in mitigation — that 2019 season, for what it’s worth, ended with defeat in the Champions League final. Before Spurs were at home with the big six, they were considered in a bracket alongside Newcastle United, Aston Villa and Everton. While Newcastle put their 56-year trophy wait behind them with their Carabao Cup success last month, they had to go down to the Championship first. Villa were also relegated in 2015-16.
While those sides struggled, Tottenham worked their way into contention. Jibes about the trophy wait, however, are the go-to method for poking fun at a club that has broadly overachieved over the past decade or so given their spending relative to many of their rivals.
Still, Spurs’ 17-year wait for a trophy is startling. There have been seven semi-final and four final defeats since Spurs beat Chelsea in the League Cup final in 2008. Over that time, their average league position was 4.94, basically fifth.
Since the resumption of competitive football after World War II, no club in England has had a higher average league position over a 16-year period than Tottenham’s between 2008-09 and 2023-24 and not lifted any kind of silverware. It’s an incredibly unlikely combination.
You only need look at Manchester United by way of comparison. Spurs have finished above United in six of the 11 full seasons since Sir Alex Ferguson’s retirement, yet during that spell United have so far won five major trophies to Tottenham’s none.
Premier League
While the 2016-17 side was undoubtedly better equipped to compete for a title, Antonio Conte’s Chelsea were more consistent. Between October 1 and December 31, Chelsea won 13 straight Premier League matches, creating a 13-point gap between them and Tottenham, who were fifth at the time. Though Spurs went on a dominant run of their own, winning 13 of their final 15 league matches to finish with 86 points, Chelsea closed the season out strongly to win the title, finishing seven points ahead of their London rivals.
Had Tottenham replicated that total the previous season, they would have won the title by five points.
Though Spurs may not have been entirely ready to compete at the elite level, the 2015-16 season represents somewhat of a missed opportunity. Tottenham were slow to get out of the blocks, picking up three draws and a defeat in their opening four matches. Failure to turn draws into wins would be the defining feature of their season, picking up 13, the most of any side in the top six. Still, Spurs were young and inexperienced — Harry Kane, Son Heung-min, Christian Eriksen and Dele Alli were all 23 or under at the start of the season — and were not expected to produce a title challenge.
Without any standout competitor, Leicester City lifted the league title as fairytale champions. Despite the pain, it should be remembered that Spurs had bettered all pre-season expectations by finishing as high as third.
Verdict: Spurs weren’t ready to compete for a league title in 2015-16 and came up against a slightly more consistent Chelsea side in 2016-17. When will they next get a better chance?
FA Cup
Spurs have reached the semi-final of the FA Cup four times since their last trophy and have not reached the final since 1991 — but they probably should have done so.
The standout example was in 2009-10, with Harry Redknapp’s side facing Portsmouth, who became the Premier League’s first club to enter administration. Not only were they in dire straits financially, but the south coast side were terrible on the pitch too, having been marooned at the bottom of the table since matchday two. To his credit, Redknapp did not overlook his former side, naming a full-strength squad for the Wembley occasion, but Spurs could not find a breakthrough in 90 minutes, and the tie went to extra time.
Portsmouth shocked Spurs, first through Frederic Piquionne, who capitalised on a Michael Dawson slip to put Avram Grant’s side ahead before former Spurs man Kevin-Prince Boateng punctuated Spurs’ most painful FA Cup defeat of the decade.
Spurs have been handily beaten twice by Chelsea in FA Cup semi-finals, but not without controversy.
Two years after the Portsmouth defeat, Chelsea beat Tottenham 5-1 at Wembley, but it may have turned out differently had goal-line technology been introduced by that point. With Chelsea 1-0 ahead, Juan Mata had a shot blocked by bodies on the line, but referee Martin Atkinson awarded a goal. Gareth Bale scored minutes later to make it 2-1, but the west Londoners ended the affair comfortable winners.
“I spoke to (Atkinson), and he said he feels worse than I do about it,” said Redknapp after the game. “I said, ‘I don’t think so’.”
In 2016-17, Spurs and Chelsea met as the two best teams in England, and Chelsea came out on top, winning 4-2. Losing to the best team in the country is excusable, but Pochettino’s decision to forgo the style that had brought Spurs into contention and match Conte’s system, starting Son at left wing-back, remains puzzling to this day.
Since Chelsea last won the league title (2016-17), the west Londoners have added four major trophies (FA Cup, Champions League, Club World Cup and the Europa League) to their cabinet. Between 2017-18 and 2023-24, they averaged 65 points a season. Spurs, for comparison, averaged 67.
Chelsea’s anomalous 12th-placed finish in 2022-23 skews the results. Still, it indicates how Spurs have provided consistent competition with their so-called “Big Six” counterparts in the league but have fallen well short from a trophy perspective.
A similar analysis can be made against Manchester United, who beat Spurs, with Michel Vorm in goal instead of Hugo Lloris, in the semi-final in 2017-18. In the years post-Sir Alex Ferguson, Tottenham (68.6) averaged a marginally higher points tally than United (68.1). However, United have won five trophies (Europa League, two FA Cups and two League Cups).
Verdict: There’s no doubt Spurs should have beaten Portsmouth at Wembley in 2010, but defeats by Chelsea sting for different reasons. Honourable mentions include the FA fifth-round defeat against understrength Championship side Sheffield United in 2022-23, the fifth-round penalty shootout defeat by Norwich City in 2019-20, and the 2-1 fourth-round defeat by Championship Leeds United in 2012-13.
League Cup
Spurs have lost in the final of the League Cup three times in this period, but all against better teams: Manchester United in 2008-09, Chelsea in 2014-15 and Manchester City in 2020-21.
The City defeat is perhaps the most contentious, a final often remembered in relation to Jose Mourinho, despite not being in the dugout for Spurs that day. Days before, he was sacked and replaced by a 29-year-old rookie Ryan Mason. We won’t ever know whether it would have made much of a difference, given City won their fourth successive Carabao Cup with a 1-0 win, but the decision to replace a serial winner with experience of underdog triumphs continues to be contested. In Levy’s defence, Mourinho had presided over a Europa League collapse against Dinamo Zagreb the month before.
Still, Spurs have failed to capitalise on straightforward opportunities earlier in the tournament. Chief among the disappointments was the penalty shootout defeat by League Two Colchester United in 2019-20. Pochettino was sacked weeks later, the 17th and final time the Argentinian presided over a cup exit as Spurs boss.
Verdict: In the drought period, the League Cup has been Tottenham’s most consistent cup tournament. There should be no great shame in losing to better teams in the final but defeats against Colchester, Norwich in 2012-13 and West Ham United in 2017-18 (after leading by two goals) were missed opportunities to win their fifth League Cup.
European competition
While it’s impossible to look back on the 2019 Champions League final without a tinge of regret, Tottenham lost 13 games in the Premier League that season and were coming towards the end of their cycle under Pochettino.
Having reached the final for the first time in the club’s history with a half-fit Harry Kane leading the line against a Liverpool side that would be a fair match for almost any club side in history, the journey to Madrid — chiefly the second legs away at Manchester City and Ajax — represents cherished memories rather than a trophy opportunity squandered.
However, there remains a feeling the Champions League campaigns in 2016-17 and 2017-18 ended prematurely, given the strength of the Spurs side at the time.
Tottenham thrilled in the 2017-18 group stage, collecting five wins and a draw from their six matches to top the table. Spurs beat Borussia Dortmund home and away, but the highlight of the phase was a 3-1 home win over eventual winners Real Madrid.
Still, Juventus eliminated them in the first knockout phase — the tie remembered by Giorgio Chiellini’s, “It is the history of Tottenham” comments after the second leg. After clawing back a 2-0 deficit in Turin, taking two away goals back to London, Spurs lost 2-1 at Wembley after conceding two goals in the final 26 minutes.
The season before, Spurs failed to progress out of a group with Monaco, Bayer Leverkusen and CSKA Moscow. It didn’t stop there, however, as Spurs were knocked out of the Europa League Round of 32 — which they qualified for by finishing third in that Champions League group — by Gent, who sat eighth in Belgium at the time. For context, Spurs finished on 86 points in the Premier League in 2016-17.
Perhaps their best chance of winning the Europa League came in 2012-13, when Gareth Bale helped fire them to a then-best Premier League points tally, but Andre Villas-Boas’ side couldn’t overcome Swiss outfit Basel (featuring a young Mohamed Salah) in the quarter-finals.
Verdict: In the pantheon of European underachievements since 2008, the Gent debacle ranks at the top of the list, given how good Spurs were at the time. Honourable mentions include finishing behind Rubin Kazan and PAOK in their Europa League group in 2011-12, the Mislav Orsic hat-trick in the second leg of the Europa League round of 16 in 2020-21, and losing 2-1 away at Slovenian side Mura in the 2021-22 Europa Conference League.
(Top photos of Gareth Bale and Son Heung-min; Getty Images)