How Long It's Been: Tottenham Hotspur Won a Trophy

Of course, they released a DVD.

Note: This was first written on February 24, 2018, the 10th Anniversary of the previous occurrence, and has been updated.

Yesterday, May 21, 2025, a date which will live in infamy, Tottenham Hotspur won a trophy.

They won the Final of the UEFA Europa League -- a tournament known from 1958 to 1971 as the Inter-Cities Fairs Cup and 1971 to 2010 as the UEFA Cup -- at Estadio San Mamés, in Bilbao, in the Basque region of northern Spain, beating fellow English team Manchester United, 1-0. Brennan Johnson scored the only goal, in the 42nd minute.

These teams somehow got to the Final of this tournament, even though, out of 20 teams in the Premier League, Man United are 16th, and Tottenham, or "Spurs," are 17.

This season, the top 5 teams in the Premier League, and the winners of the Europa League if they are not among the preceding, qualify for the UEFA Champions League, the top European tournament. In this case, those 5 teams will be League Champions Liverpool FC, Spurs' North London arch-rivals Arsenal FC, United's intra-city arch-rivals Manchester City (winners of this season's FA Cup), and, with 1 game left to decide it, 2 of these 4 teams: Newcastle United (winner of this season's League Cup), West London team Chelsea, Birmingham team Aston Villa, and East Midlands team Nottingham Forest.

The bottom 3 teams get relegated to the 2nd division of English soccer, "The Championship," and replaced by the top 2 teams and the winner of a playoff of teams 3 through 6. So, the teams finishing 18th, 19th and 20th.

In the PL, a win is 3 points, and a draw is 1 point. Newcastle, Chelsea and Villa have 66 points. Spurs have 38 points. Leicester City, in 18th place, have 25. This means Spurs are twice as close to being relegated as they are to qualifying for the Champions League the usual way.

The English media have loved Tottenham for a long time, with their 1961 team becoming the 1st in the 20th Century to win both the English top flight, then called the Football League Division One, and the Football Association Cup in the same season. This is called "doing The Double," and the Baby Boomers in England loved them for it.

When Arsenal did the same in 1971, it was a different time. The Boomers had grown up, and this Arsenal side was a side for their kids, or maybe their younger brothers.

Unless you were raised in a family that loved Arsenal, you were raised to hate Arsenal - as if the two were the only teams in London. There are 12 League clubs within the M25, London's version of a road "beltway," and usually half of those are in the top flight, now called the Premier League.

When Arsenal had a run of success, 1987-94 (2 League titles, an FA Cup, 2 League Cups and the now-defunct European Cup Winners' Cup), they were not loved by the public outside North London as the 1981-84 "Spurs" side were (winning 2 FA Cups and a UEFA Cup).

When Arsenal became perhaps the greatest team in English history between 1998 and 2006 (3 League titles, 1 unbeaten, 4 Cups, 2 of them as part of Doubles), they gained admirers all over the world, thanks to the growth of satellite TV coverage. But, despite winning next to nothing, Spurs always got the more flattering coverage in the media.

As a result, when Arsenal lost the 2011 League Cup Final, that made it 6 years since they'd won a trophy. They won the 2005 FA Cup, but haven't won the League since, lost the UEFA Champions League in the 2006 Final and the 2009 Semifinal; lost the FA Cup in the 2009 Semifinal; and lost the League Cup in the Final in 2007 and 2011, and in the Semifinal in 2008 - which brings me to today's focus.

The League Cup is kind of a weird competition. All 92 clubs in the Football League, in all 4 divisions, are eligible for it. This makes it different from the FA Cup, where every Club in England, and, through an arrangement, a few teams in Wales, are eligible for it. That's over 700 teams.

Each round is a single match, with home field advantage chosen by a lottery, until the Semifinal. Then, it's 2 legs, home-and-home. The Final, as is that of the FA Cup, is held at Wembley Stadium in West London, England's national stadium.

The FA Cup was founded in 1871. The League Cup was not founded until 1960, and thus has considerably less prestige. For a club with the kind of support that Tottenham have, winning it would be huge. For a club with the kind of support that Arsenal have, winning it would be nice, but there are more important things, and they are - at least, theoretically - within reach.

This is not the case with Tottenham. They have not won the league, under any name, since that 1961 Double. They have had close calls the last 2 seasons, but blew it - or, as they say in England, "bottled it" - both times.

Indeed, late-season collapses have happened to Spurs several times in recent years. The template was 1987. When they took the field (or "the pitch") at their former home of White Hart Lane at a Semifinal replay of the League Cup on March 4, they had a chance at a unique domestic "Treble": Winning the League, the FA Cup, and the League Cup in the same season.

But Arsenal won that game, and the Final against Liverpool. Spurs fell apart in the League, and choked in the FA Cup Final. In a span of 73 days, they went from a good chance at a unique feat to having won nothing.

(Manchester United won a "European Treble" in 1999: The League, the FA Cup, and the Champions League. Others teams have done this in other countries, but not in England. Manchester City won a domestic Treble in 2021, and a European Treble in 2023.)

In 2006, 2012 and 2013, Spurs had a great chance to finish ahead of Arsenal. Each time, they were ahead going into the last game of the season. And, each time, the results didn't go their way. They did not finish ahead of Arsenal between 1995 and 2017. (The 2006 occurrence is the most notable. One does not simply discuss "The North London Derby" without mentioning that occurrence. It is folly.)

In 2007, the North London rivals met in the League Cup Semifinal. In the 1st leg, at The Lane, Spurs blew a 2-0 lead, and it ended 2-2. In the 2nd leg, at Arsenal's new Emirates Stadium, it was 1-1 after regulation. Away goals didn't matter, so extra time (we would say "overtime") was played, and Arsenal quickly scored twice to win 5-3 on aggregate.

In 2008, the situation was reversed. Until this season, Arsenal manager Arsène Wenger has played mainly reserves in the League Cup, trying to get them experience for more prestigious games. The 1st leg was at the Emirates, and it was a 1-1 draw. The 2nd leg, at The Lane, was no contest, as Tottenham, mainly starting their starters against "Arsène Wenger High School," won 5-1.

Spurs soon released a DVD of this game, titled The Perfect Game. A, It was starters against reserves. Big deal. B, How can it be "perfect" if you let in a goal? Morons.

February 24, 2008: Tottenham beat West London club Chelsea 2-1 to win the League Cup at Wembley Stadium. Although Didier Drogba, a.k.a. "Dogbreath," another of the most hated opponents Arsenal have ever had, due to his goals against them and his obvious and unrepentant diving, opened the scoring, Tottenham got a penalty that was buried by Dimitar Berbatov, the Vulgarian Bulgarian, and the game went to extra time. Jonathan Woodgate, a defender, scored the winner in the 94th minute.

Spurs fans acted like they'd won the League and the Cup - instead of just the League Cup. It was their 1st trophy of any kind since the 1999 League Cup. Those are the only 2 trophies they've won since their last FA Cup win in 1991, and they haven't even been to a Final in that tournament since, going 0-4 in Semis, including 0-2 against Arsenal. And that 1961 League title remains their last.

As Arsenal's trophy drought grew, to 7 years, 8 years, 9 years, before it finally ended at 9 with the 2014 FA Cup, the English media harped on it more and more. "Arsenal's trophy drought" became a catchphrase, a cliche, a meme.

Spurs have now surpassed that. But did anybody talk about "Spurs' trophy drought?"

No, because that only happens to big clubs. When Manchester United went 26 years without winning the League, from 1967 to 1993, it was talked about constantly. Liverpool went 30 years without winning the League, from 1990 to 2020, and it was talked about constantly.

And now that Arsenal have gone 21 years without winning the League, since 2004, it is talked about constantly. Just as it was from 1971 to 1989, when, to borrow the phrase of author and Arsenal fan Nick Hornby, it was "Eighteen fucking years!" And when Arsenal reached the climax of the 1971 season, before winning both the League and the FA Cup that year for "The Double," their last trophy was the 1953 League title, right before Queen Elizabeth II was crowned, and they said, "Arsenal haven't won a trophy since the Coronation."

So, big clubs get this treatment. Tottenham don't. That's because Tottenham are not a big club.

Oddly, it was their recent "world-class" striker, Harry Kane, who was mocked for not winning a trophy, for club or country. Even after he left for Bayern Munich, the biggest sports team in Germany, in his 1st season with Bayern, they didn't win a trophy. Finally, they won the Bundesliga this season, and so, like his former team, Kane finally won a trophy.

But Spurs are a club that didn't win a trophy for 18 years, 2 months and 25 days -- 6,296 days. How long has that been?

*

At the time, Molson Coors, which owns the London-based Carling brand of beer, held the naming rights to the tournament. From 2003 to 2012, it was known as the Carling Cup. Previously, another brewery had it 2004-12: The Worthington Cup. This was a far cry from 1982-86, when Britain's national Milk Marketing Board had it and it was the Milk Cup; or 1993-98, when it was the Coca-Cola Cup.

Betting company Littlewoods held it 1986-90, the now-defunct electronics company Rumbelows 1990-92, Capital One 2012-16, no sponsor last year (it was just "The EFL Cup," for "English Football League"), and now, Thai-based (but Brazilian-sounding) energy drink Carabao: The Carabao Cup.

Of the 16 players Tottenham named as possibilities for use in that game, only one ever won another trophy with an English team, Dimitar Berbatov with Man United. Most of the others, including "Spurs legends" Ledley King (nicknamed "Leadfoot Queen" by Arsenal fans), Tom Huddlestone (known as "Hundredstone" for his hefty weight), Robbie Keane, Jermaine Jenas and Aaron Lennon had long and frustrating careers. And manager Juande Ramos was fired early in the 2008-09 season.

Tottenham have since torn down White Hart Lane, and moved into a new stadium, still named Tottenham Hotspur Stadium. The joke is that, after years of playing in a stadium that Arsenal fans called "The Shithole," they built a stadium that actually looks like a toilet bowl.

On February 24, 2008, Manchester United were then the holders of the Premier League title, and were about to win it again. Chelsea were the holders of the FA Cup, and were about to be succeeded as such by Hampshire club Portsmouth. Man United would beat Chelsea in the Final of the UEFA Champions League -- which, like the Super Bowl, is selected in advance, in the hope of getting a neutral site. So these 2 big English clubs faced each other for the championship of Europe in... Moscow. Man U succeeded AC Milan.

Neymar and Kevin De Bruyne were 16 years old, Son Heung-min and Mohamed Salah were 15, Harry Kane and Paul Pogba were 14, Christian Pulisic and Declan Rice were 9, Gianluigi Donnarumma was about to turn 9, Ebereche Eze was 8, Erling Haaland was 7, Bukayo Saka was 6, and Myles Lewis-Skelly was a year and a half.

Current Tottenham manager Ange Postecoglu was managing Panachiki FC in Greece. Current New York Red Bulls manager Sandro Schwarz was playing for Wehen Wiesbaden in Germany. Current New York City FC manager Pascal Jensen was coaching with Sparta Rotterdam in the Netherlands.

Tom Tibodeau of the Knicks was an assistant coach for the Boston Celtics. Brian Daboll of the Giants was the quarterbacks coach for the Jets. Alain Vigneault of the Rangers was an assistant coach for the Tampa Bay Lightning. Patrick Roy, the legendary goaltender now the head coach of the Islanders, was head coach of the minor-league Quebec Ramparts. Sheldon Keefe of the Devils was head coach of the minor-league Pembroke Lumber Kings. Jordi Fernández of the Nets was working at a basketball academy in his native Spain. Aaron Glenn of the Jets was in his final season as a player, with the New Orleans Saints. Aaron Boone of the Yankees was playing for the Washington Nationals. And Carlos Mendoza of the Mets was playing for the Trenton Thunder, then the Class AA farm team of the Yankees.

In North American sports, the defending World Champions were the Spurs -- San Antonio, not Tottenham -- the New York Giants, the Boston Red Sox *, the Anaheim Ducks, and the Houston Dynamo were the holders of the MLS Cup. The Heavyweight Champion of the World, depending on who you believe, was either Ruslan Chagaev (recognized by the WBA), Oleg Maskaev (WBC), or Wladimir Klitschko (IBF).

The Olympic Games have since been held in Britain, Canada, Russia, Brazil, Korea, Japan, France, and China twice. The World Cup has since been held in South Africa, Brazil, Russia and Qatar.

The Mayor of London was Ken Livingstone. The Prime Minister was Gordon Brown. The current holders of those offices, Sadiq Khan and Theresa May, respectively, were both then serving in the House of Commons. Queen Elizabeth II was the monarch -- that hasn't changed.

The President of the United States was George W. Bush. Barack Obama was running to replace him. So was Joe Biden. The idea that Donald Trump could become President, or that any President would do the things he's done, and say the things he's said, was ridiculous -- and should have stayed that way.

The Governor of New York was Eliot Spitzer -- for another 22 days. Kathy Hochul was the Clerk of Erie County (which includes Buffalo). The Mayor of New York was Michael Bloomberg. Eric Adams was in the New York State Senate. The Governor of New Jersey was Jon Corzine. Phil Murphy was National Finance Chair of the Democratic National Committee.

The Pope was Benedict XVI. The current Pope, Leo XIV, was then Robert Francis Prevost, Prior General of the Order of Saint Augustine. The Prime Minister of Canada was Stephen Harper. The holder of the Nobel Peace Prize was former Vice President Al Gore, for his work to stop the ill effects of climate change -- which is one of several examples of the Nobel Committee showing the need for separate awards for Peace and Humanitarianism. While Gore certainly deserved an award, what he got this one for had nothing to do with either preventing or stopping a war. There have since been 4 Presidents of the United States, 7 Prime Ministers of Britain, and 3 Popes.

There were still living veterans of World War I; the subsequent civil wars in Germany, Poland, Russia and Finland; the Mexican Revolution, the Turkish War of Independence, Mussolini's March On Rome, and the Brazilian Revolution. There were still living people who had survived the sinkings of the RMS Titanic, the RMS Lusitania, the SS Morro Castle, the SS Eastland, the USS Panay, the HMS Hood and the USS Juneau.

All 7 of J.K. Rowling's Harry Potter books had been published, but only the 1st 5 films had been made. Later in the year, Suzanne Collins would publish The Hunger Games. George R.R. Martin had published the 1st 4 A Song of Ice and Fire books, but Game of Thrones had yet to debut on television. Same with The Walking Dead, which had, at that point, only existed in comic book form.

Films premiering in the late Winter of 2008 included Cloverfield, Mad Money, The Other Boleyn Girl, Will Ferrell's 1970s basketball film Semi-Pro, and the 4th (but not the last) Rambo film. Daniel Craig was James Bond, Brandon Routh was Superman, Christian Bale was Batman, and David Tennant was The Doctor.

Girlfriends aired its last first-run episode. Keeping Up with the Kardashians, Breaking Bad and Terminator: The Sarah Connor Chronicles had recently debuted. No one had yet heard of Richard Castle. The Number 1 song in America was "Low" by Flo Rida (Tramar Lacel Dillard) and T-Pain (Faheem Rashad Najm). Michael Jackson was still alive.

Inflation was such that what $1.00 bought then, $1.52 would buy now -- or, more to the point of the country in question, £1.00 then is about £1.71 now. A U.S. postage stamp cost 41 cents, and a New York Subway ride $2.00. The average price of a gallon of gas was $3.32, a cup of coffee $2.45, a McDonald's meal (Big Mac, fries, shake) $6.39, a movie ticket $7.20, a new car $23,429, and a new house $290,400. The Dow Jones Industrial Average closed the preceding Friday at 12,381.02.

The tallest building in the world was Taipei 101 in Taiwan. The age of social media was well underway, but, as yet, there was no Pinterest, no Instagram, and no iPad. Sony PS3 and Wii were battling it out to be the leading home video game system.

In the Winter of 2008, Cyprus and Malta adopted the euro as their currency. The Kivu conflict in the Democratic Republic of the Congo was ended by a peace deal. Iran launched its 1st rocket into space; 18 years later, they have not yet had any manned missions. Kosovo declared independence from Serbia. Prime Minister Kevin Rudd of Australia issued a formal apology to the Stolen Generations, Aboriginal children taken from their families to be raised "white" for much of the 20th Century.

And the subprime mortgage crisis resulted in stock markets around the world crashing on January 21, and again on February 5. The Great Recession was underway, but few people suspected that it would get as bad as it did later in the year. Indeed, at this point in the 2008 Presidential election, both the Republican candidates, led by Senator John McCain of Arizona, and the Democratic candidates, led by Senators Hillary Clinton of New York and Barack Obama of Illinois, had foreign policy matters, especially the ridiculous Iraq War, as their main focus.

Mount Everest conqueror Sir Edmund Hillary, and chess legend turned conspiracy theorist Bobby Fischer, and 1950s FA Cup hero Jimmy Dugdale died.

Most of the famous people born in 2008, who turn 17 in 2025, are "stars" on YouTube and TikTok. Cameron Crovetti, who plays Ryan, Homelander's son on The Boys, was born on March 12. Iain Armitage (who played the title role in Young Sheldon) was born on July 15. Sunny Sandler, who has followed her father Adam into acting, was born on November 2.

February 24, 2008. Tottenham Hotspur won a trophy, the Football League Cup, then known as the Carling Cup, defeating Chelsea 2-1 at Wembley Stadium.

It took them 18 years and nearly 3 months to win another trophy. In the interim, arch-rivals Arsenal have won 4 FA Cups.

Tottenham are the biggest joke franchise in sports -- any sport, any country. Here's a joke:

A mistake was made, and a game against Tottenham was scheduled for the same day that Arsenal were away in the Champions League. Arsène Wenger tells his players, "Boys, go, and leave Tottenham to me. I will play them all by myself."

So the team goes to the Continent, and, at halftime, they check their phones, and see: "HT: Tottenham 0-1 Arsenal, Arsène Wenger 10'." That gives them the boost they need, and they win their game. But when they're done, they see "FT: Tottenham 1-1 Arsenal, Arsène Wenger 10', Aaron Lennon 90'+4."

The Gunners get back home, and they see Wenger, still in his kit, sitting on a bench, head in his hands. He looks up, and says, "Boys, I let you down." They say, "What are you talking about? You held them off for 93 minutes, all by yourself. Even at the end, they only managed a draw. You even scored in the 10th minute."

"Yes," Wenger says, "but I got sent off in the 12th."

Tottenham: A joke forever.