It’s been 13 years since Tottenham Hotspur won a trophy, when they beat Avram Grant’s Chelsea side 2-1 after extra-time at Wembley Stadium.
It was supposed to be the start of something fruitful and successful, but instead it turned into a one and done. The special era that consisted of players such as Robbie Keane, Dimitar Berbatov, Ledley King and others won just the sole pot of silverware.
Now as we enter a new year, Spurs have a chance to make their first cup final since that day in 2008 when they take on Brentford in the Carabao Cup semi-final on Tuesday night.
In a slightly different layout to usual, the semi-final stage will take place as a one-off game this year instead of the usual two-legged final four.
It means that Mourinho’s side need to navigate a home fixture against another London side, who currently reside in the division below them.
The Portuguese boss has an affinity with the League Cup. He has won the tournament on four separate occasions, including during both of his tenures as Chelsea boss.
It’s always been his way of showing everyone that his process is working and instilling confidence in his players ahead of the season run-in. This year will be more different still, with the final now taking place in April instead of it’s usual spot in the final weekend of February.
Should Mourinho win the tournament, it will be seen as a success for the club. But is it?
With a new, shiny £1bn stadium and a squad worth hundreds of millions of pounds, is a League Cup that other clubs don’t take nearly as seriously as they do other competitions really that successful?
It’s certainly a start. You need to win trophies to breed a winning mentality, something that Mauricio Pochettino never quite managed. The club need to show the top players entering their prime years that they’re serious about progressing and becoming a club that wins trophies, not just challenges for them.
Harry Kane has specifically said for years that he wants to win trophies and as the England skipper turns 28 later this year, he is still yet to lift any type of silverware.
Rumours have begun circulating that the biggest clubs in the world are eyeing up a potential move for him and there’s only so long he can go before he seriously considers the move.
Mourinho was brought into the club to win and this is the best chance he has of doing so this season. The league table right now is tight, with any sort of good run of form likely to put you towards the top of the table.
But Spurs should be content to walk before they can run. They have the talent to win the league in the squad, but it shouldn’t be an expectation.
A win against Brentford will have the fans dreaming of silverware once again, and this time they’ll be hoping that it will be the start of an era of success rather than another one and done.