When Was The Last Time Tottenham Won A Trophy?

Photo Credit: AP

When was the last time a Tottenham won a trophy? It’s probably a question that haunts Spurs fans. But with a proven winning manager at the helm and a strong start to the new Premier League season, will Tottenham be able to end their long wait for silverware sooner rather than later?

Exactly when was the last time Tottenham won a trophy? They haven’t had their hands on a piece of silverware in more than three decades. Will current Tottenham manager Antonio Conte be the one to succeed where so many before him have failed and snap that long barren spell for the club? Perhaps all the pieces will finally come together for the Lilywhites.

When Was The Last Time That Tottenham Won A Trophy?

Tottenham last put silverware into their cabinet with a victory over London rivals Chelsea in the 2008 Football League Cup Final. Spurs had been underdogs on the day, but they came good as they overturned a first-half deficit.

Chelsea forward Didier Drogba had put the Blues in front six minutes before the half-time break and looked in control. But deep into the second half, Tottenham were handed a lifeline when they were awarded a penalty kick.

Dimitar Berbatov slotted it home, taking the match to extra time. Depositing having less possession and fewer shots on target in the match, Tottenham came up with a winner. It was through defender Jonathan Woodgate who took a second bite of the cherry to head the ball past Chelsea keeper Petr Cech. The success ended a nine-year trophyless run at the time for Spurs.

That was Tottenham’s fourth League Cup title, adding to successes in 1971, 1973 and 1999.

The 1991 FA Cup Final

What about the FA Cup? When was the last time that Tottenham won a trophy in that competition? That was in the 1991 FA Cup Final when Spurs lined up against Nottingham Forest at Wembley for one of the greatest football matches. Things didn’t start well for Spurs at Wembley as Forest opened the scoring after a quarter of an hour through Stuart Pearce.

But a strong second half saw the Lilywhites claw their way back into the match, Paul Stewart levelling up the match, sending it to extra time. The match was settled when Nottingham Forest defender Des Walker put through his own net.

Some famous players from Tottenham’s history lined up in that match, including centre forward Gary Lineker. His former England teammate Paul Gascoigne was in the starting eleven along with the likes of Gary Mabbutt and Paul Allen. Terry Venables, who had been in charge at La Liga giants Barcelona before taking over at Tottenham, was the manager.

Spurs Create History in ’91

That 1991 success was a big moment for Tottenham as they set a new standard in FA Cup victories. That win was their eighth, the first club to reach that number. However, with their stagnation in the three decades since, they have been caught by Chelsea and Liverpool and have been surpassed by Manchester United (12) and their great rivals Arsenal (14).

Spurs have not even been back to the FA Cup Final since that most recent winning year. The 1991 success also continued a very peculiar trend with the club and its relationship with silverware. Each of Tottenham’s seven domestic titles in their history have been won in a year ending with a 1.

They couldn’t answer the question of when was the last time Tottenham won a trophy by earning one in 2021. The London club will be hoping that they don’t have to reach the start of the next decade to have the next realistic chance of snapping this winless streak.

Tottenham’s League Titles

Tottenham have been crowned English champions twice before. They got their breakthrough in the 1950/51 season of the top tier, which was then the old First Division. Tottenham took the title by four points ahead of Manchester United.

That same season saw Blackpool finish third in the English top flight which also contained the likes of Portsmouth, Bolton and Charlton. Chelsea survived relegation in the 1950/51 season by goal average, which was used as a tie-breaker back then.

Tottenham would double their tally of League titles a decade later. They claimed the 1960/61 crown by eight points ahead of Sheffield Wednesday. That was a big year for the Lilywhites as they compiled a domestic double by lifting the FA Cup as well.

Tottenham’s Eight FA Cup Wins

The Missed Premier League Title Chance

The Premier League is a tougher title to win than the FA Cup and League Cup is likely to be. Especially with the evolution of the game since the 1990s and the money that the likes of competitors Chelsea and Manchester City among others, can throw around.

Back in the 2015/16 Premier League season, Tottenham had their best chance ever of winning their inaugural Premier League title. It was, unfortunately for their fans, a chance that went desperately begging.

The 2015/16 Premier League season was a strange one overall. The usual suspects like Chelsea, Manchester City, Manchester United and Liverpool were nowhere near the title picture that season.

It boiled down to North London rivals Tottenham and Arsenal, trying to reel in the surprise package that was Claudio Ranieri’s Leicester City. With just four games of the season remaining Tottenham were in the hunt for the title.

They had just put together a hot run of form with four wins in five (D1) and looked as if they may go the distance and put Leicester under pressure. But Tottenham’s momentum was halted in a shock 1-1 home draw against West Brom.

The Famous Battle At The Bridge

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Chelsea’s Eden Hazard, centre, competes for the ball with Tottenham’s Toby Alderweireld, left, and Kyle Walker, right, during the English Premier League soccer match between Chelsea and Tottenham Hotspur at Stamford Bridge stadium in London, Monday, May 2, 2016. (AP Photo/Frank Augstein)

The draw meant that Tottenham then went to rivals Chelsea in a must-win match at Stamford Bridge. It was a nasty, ill-tempered game, in which remarkably there was no red card shown. Emotions were high, over-the-top tackles were flying around and at the half-time break, Tottenham’s travelling fans were on Cloud Nine.

First-half goals by Harry Kane and Son Heung-min had put Mauricio Pochettino’s Lilywhites in firm control of the match. But they weren’t prepared for what hit them in the second half, notably Chelsea’s Eden Hazard rising to the occasion. The Blues pulled a goal back early in the second half through Gary Cahill.

With less than ten minutes to go, Tottenham just had to hold on. They just had to survive any way that they could to pick up the three points in the title race. But some neat interplay with teammate Diego Costa saw Hazard round off a move by hooking the ball into the top corner with just seven minutes to play.

Just twelve months earlier Eden Hazard had won the league title for Chelsea. His late intervention at Stamford Bridge in Chelsea’s dramatic and heated comeback handed Leicester the shock Premier League title. It ruined Tottenham’s dreams. Spurs lost their final two matches of the season to finish third.

How Many Trophies Have Tottenham Won?

First Division/Premier League (2)
Second Division/Championship (2)
FA Cup (8)
League Cup/EFL Cup (4)
FA Charity Shield/Community Shield (7)
UEFA Cup Winners’ Cup (1)
UEFA Europa League (1)

Can Conte Crack It?

Having had a successful managerial career in Italy’s Serie A with Juventus and Inter Milan, Tottenham gave Antonio Conte a managerial contract in November 2021. The former Chelsea manager took a while to settle in at the club after he took over from the short-lived spell of Nuno Espírito Santo.

But slowly and surely things came together for Conte at Tottenham. The Italian guided Tottenham to a fourth-place finish in the 2021/22 Premier League season. That put them back in the UEFA Champions League for the first time in two seasons. It was a good reward for the club, but they were a long way behind the top two of Man City and Liverpool on points.

Conte is a taskmaster and a winner. He is a four-time Serie A winner, three with Juventus and one with Inter. He also guided Chelsea to the 2016/17 Premier League title in his first season in England.

With Tottenham making a very solid start of six-matches unbeaten at the start of the 2022/23 Premier League (matching reigning Champions Man City’s points haul at the same stage), can Tottenham fans start believing again? Is the drought about to end?

Does The UEFA Champions League Offer Tottenham A Chance?

Could the UEFA Champions League be the path to Tottenham’s silverware? In limited appearances in the competition, they have done alright in the competition. Spurs reached the quarter-finals in 2011 and the 2019 Final.

Tottenham met fellow Premier League side Liverpool in the 2019 Champions League Final. With the Reds being awarded and successfully converting a penalty early just a couple of minutes into the match. Tottenham really never got to play the Final that they wanted to .

It was another big chance of silverware that slipped through their fingers. But they have shown that they can knock on the door. They just need someone to lead them through it. Conte could be that man.

Timing Is Everything With Kane

Harry Kane, one of the top strikers in the world and who holds the most goals for a single Premier League club, turned 29 years old in the summer of 2022. The England captain desperately tried to leave the club ahead of the 2021/22 season but stayed.

When he turns 30 in the summer of 2022, he will be in the final year of his contract at Tottenham. That means the club, if they can’t convince him to stay, will risk losing him for nothing at the end of the season. That will dominate Tottenham news next summer.

But Kane is still a Tottenham player and has continued to score. He is the focal point of their team and Tottenham fans will likely know that the key to their club getting their hands on a trophy will likely need to happen soon. Basically with Harry Kane’s time frame at the club.

He’s won the Premier League Golden Boot three times and that’s an asset Tottenham have to make the most of. It feels like a case of now or never for the Lilywhites. A chance for Tottenham fans to put an end to the pain of hearing, when was the last time Tottenham won a trophy?