Tottenham Hotspur’s defeat to AC Milan in the Champions League Round of 16 means that the club will almost certainly go yet another season without winning a trophy.
The European exit at the hands of the Italians came exactly a week after they were dumped out of the FA Cup by Championship side Sheffield United.
Spurs only made it as far as the third round of the Carabao Cup, while they are all but out of Premier League title contention and are instead in a battle to qualify for the Champions League again next season.
But exactly when was the last time Tottenham added a new piece of silverware to their trophy cabinet?
Read on to find out.
When did Tottenham last win a trophy?
Tottenham last won a trophy in 2008 – an incredible 15 years ago when Juande Ramos was the manager.
The north Londoners beat Chelsea in the League Cup final courtesy of a 2-1 win in extra-time at Wembley.
Didier Drogba had opened the scoring for Chelsea just before half-time, but Spurs responded with 20 minutes left on the clock thanks to a penalty from Dimitar Berbatov.
Jonathan Woodgate then popped up to score the winner in the fourth minute of extra-time to hand Tottenham their fourth victory in the competition.
At the time, it was Tottenham’s first trophy for nine years, meaning they have only won one trophy since the turn of the new millennium.
Have Tottenham ever won the Premier League?
No, Tottenham are yet to get their hands on the Premier League title.
Their best results in the competition are third and second place in the 2015/16 and 2016/17 seasons respectively under the management of Mauricio Pochettino.
The 2015/16 season saw them chase down Leicester City in the hunt for the title, with a late collapse seeing them instead finish behind arch-rivals Arsenal in third.
They did go one better the following season, eventually finishing seven points behind winners Chelsea – who were managed by none other than current boss Antonio Conte.
First appear at When was the last time Tottenham won a trophy?