Tottenham's worst defeats since winning a trophy - Spurs having a bad day in the Premier League | OneFootball

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It has been 15 years since Tottenham Hotspur won their last major trophy, as the pre-season tournament ‘The Audi Cup’ does not count, even though some fans of the club may say otherwise.

Since Spurs won the League Cup in 2008 top six rivals Manchester City have won the Premier League seven times, the League Cup six times the FA Cup three times, and the Champions League once.

During this time fans of Tottenham have had to suffer some of the most embarrassing defeats in the club's history, causing lots of abuse and ridicule from rival fans.

In this list, we will be looking at the five most embarrassing defeats Tottenham have suffered since winning a trophy.

5 Fulham – 2023 League Cup Second Round

After a promising start to their season so far Spurs came into their League Cup second-round tie hoping that their fortunes would change under new manager Ange Postecoglou.

However, it appears that no matter who is in charge of the Lilywhites, they will always suffer shock (or for some people not so shocking) losses.

Spurs had a poor start to the game after early in the first half new signing Micky van de Ven scored his second own goal in four games for Tottenham, but luckily for him Brazilian striker Richarlison scored the equalizer in the second half.

This took the game for penalties, only for Colombian centre-back Davidson Sanchez to have his penalty saved by goalkeeper Marek Rodak, meaning Spurs made their earliest League Cup exit in almost two decades.

After the game, Postecoglou said to the Spurs Club Website: “We were never totally in control of the game, I don’t think they were, either.

“It was a typical cup game where both teams had their moments. In those situations, you need to take them.”

4 Liverpool – Champions League Final 2019

This loss was all the sweeter for rival fans as Tottenham were so close to winning the biggest trophy in Europe, but just fell short.

After Lucas Moura single-handedly dragged Mauricio Pochettino's side through the Champions League semi-final by scoring a second-half hattrick in the semi-final second leg against Ajax, Spurs fans thought maybe the stars would come together that year and their dreams would come true.

However, this was not the case, as Tottenham conceded a penalty only a minute into the final, causing them to go 1-0, meaning before the game had really started their trophy hopes were out the window.

And to add insult to Injury in the 87th as Divock Origi scored Liverpool’s second, adding to Tottenham’s collapse and embarrassment.

3 Southampton – Premier League

The embarrassment in this game suffered by Tottenham had less to do with the performance on the pitch, although they still came under fire for drawing 3-3 after being 3-1 against bottom-of-the-table Southampton (who were soon to be relegated).

The actual embarrassment Tottenham fans suffered was after the game when (then) manager Antonio Conte went on a sensational rant about the state of the club.

He said: “The worst situation is what was happening on the pitch. What has been happening in the last few months, what is happening in my second season.

"I think that it's the right moment to speak because I think that after this performance, for me this is unacceptable. We are winning 3-1, in control of the game, and you are able to concede two goals

“I think it's much better to go into the problem, because the problem is that for another time, we showed that we are not a team.

"We are 11 players that go into the pitch. I see selfish players, I see players that don't want to help each other and don't put their heart.

"Before today I prefer to hide this situation and to try to speak, to try to improve the spirit, the situation, with the words, with a lot of situations.

“Don't forget that in FA Cup we lost to Sheffield United, who played with young players. We were able with a strong team to be dropped from the FA Cup. And then a lot of situations, I repeat, that we are not going to improve”

Unsurprisingly after this astonishing rant the Italian manager would not manage another game for Spurs and was shortly sacked.

2 NS Mura – Europa Conference Group Stage

Despite Conte’s rant against being an incredibly embarrassing moment during his tenure at the club, it probably wasn’t his most embarrassing, that award goes to his side's 2-1 loss to NS Mura in the Europe Conference League.

Going into the tournament Tottenham were the favorites, however, they were dramatically knocked out in the group stage, predominantly due to their loss to the lowest-ranked team in the competition.

After only 30 minutes Ryan Sessegnon was sent off with his side already 1-0 down, but even after Harry Kane’s second-half equalizer and the additions of Lucas Moura and Son Heung-Min the side that sat mid-table in the Slovenian league were still able to score a 94th minute winner.

After having to forfeit their final group game because of a COVID outbreak within the squad, Tottenham were embarrassingly knocked out of the competition they really should have won.

1 Newcastle - Premier League

This match was the final game of the famous 2016/17 season that saw 5000–1 champions Leicester spectacularly win the league, 11 points ahead of the Lilywhites.

Throughout the season the Foxes were chased by Tottenham, but after the London club’s 2-2 draw with Chelsea (after being 2-0 up) allowing Leicester to win the league they completely capitulated.

This came to a head on the final day of the season when they spectacularly lost 5-1 to Newcastle, which meant they finished third in the league behind bitter rivals Arsenal, coining the term ‘third in a two-horse race’.