Tottenham Hotspur are just one game away from reaching the League Cup final, having defeated Liverpool 1-0 in the first leg of their semi-final clash.
A win or draw in the return leg at Anfield will ensure the club plays in a first cup final since the 2020/21 campaign, when they reached the final of the EFL Cup, only to lose to Manchester City.
Ange Postecoglou has come in for plenty of criticism this term, especially with the club languishing 12th in the Premier League table at the time of writing.
But could winning a first trophy since 2008 be the catalyst for improvement? The jury is still out on the Australian, but he could become the first manager to lead Spurs to a major trophy since Juande Ramos 17 years ago.
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2 ByDominic Lund
Since the Spaniard was sacked after a horror start to the 2008/09 season, the north Londoners have employed eight permanent managers. We have ranked these managers by their attempts to end Tottenham’s trophy drought.
Manager
Year appointed
Points per game
Harry Redknapp
2008
1.73
André Villas-Boas
2012
1.91
Tim Sherwood
2013
1.65
Mauricio Pochettino
2014
1.84
José Mourinho
2019
1.77
Nuno Espírito Santo
2021
1.65
Antonio Conte
2021
1.78
Ange Postecoglou
2023
1.63
8 Mauricio Pochettino July 2014 – November 2019
In hindsight, sacking Mauricio Pochettino in November 2019 was a massive mistake. Of course, the start of that season hadn’t quite gone exactly to plan, but this was a man who had led the club to the Champions League final just a few months before.
The lowest that Spurs finished in the Premier League under the Argentinian was fifth during his maiden season, qualifying for the Champions League across the next four campaigns.
In the top flight, he averaged 1.89 points per match, finishing runners-up during 2016/17, and the likes of Harry Kane and Son Heung-min developed into world-class players.
Competition
Best finish (Year)
Premier League
2nd (2016/17)
FA Cup
Semi-finals (16/17, 17/18)
EFL Cup
Final (2014/15)
Champions League
Final (2018/19)
Europa League
Round of 16 (2015/16)
7 Harry Redknapp October 2008 – June 2012
While Pochettino established Spurs as a top-four side, it was Harry Redknapp who achieved the feat first.
Taking over from Juande Ramos wasn’t easy, but the veteran manager began to slowly turn things around, going on to finish fourth during his first full season in charge, which qualified Spurs for the Champions League.
A run to the quarter-finals in the following season was mightily impressive, and while Redknapp couldn’t lead them to a trophy, the standards he set in place gave Pochettino a platform to build upon when he took over in 2014.
6 Ange Postecoglou July 2023 – present
If – and it is a big if – Postecoglou can lead Spurs to the League Cup, it may prove to be a huge turning point for the former Celtic manager.
At times, the football on show is sublime, with wins over Manchester City and Manchester United the highlights. Sticking to his attacking philosophy when some games require a more pragmatic approach may be seen as tactical naivety, but the Australian sticks to what he is good at.
Injuries haven’t helped Spurs this season, and if given time, Postecoglou could be a successful manager for the club.
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ByDominic Lund 5 Andre Villas-Boas July 2012 – December 2013
Sacked after eight months as Chelsea manager didn’t deter André Villas-Boas from trying again in the Premier League, this time with Spurs.
During the 2012/13 season, he led the club to a fifth-place finish, perhaps over-relying on Gareth Bale’s brilliance at times, but the football on show was superb.
They scored 70 goals that term in the Premier League – the fifth-best attacking side in the division – but this wouldn’t save Villas-Boas.
Indeed, he was sacked in December 2013 after a 5-0 defeat to Liverpool, ending his 18 months back in England.
4 Antonio Conte November 2021 – March 2023
Antonio Conte took over the club in November 2021 following the sacking of Nuno Espírito Santo and led the club to fourth place, losing just six games in the process.
Despite this, Spurs failed to make it past the last 16 in the Champions League during 2022/23, while Conte lasted until March 2023 before being sacked after a run of one win in his previous five matches.
3 Tim Sherwood December 2013 – June 2014
Tim Sherwood lasted just 26 matches in charge of Spurs, but he did have a 59% win percentage in the Premier League.
While the football wasn’t the greatest under the Englishman, his commitment to giving youth talent a chance has to be recognised.
Indeed, it was Sherwood who gave Kane his first-ever start in the Premier League. 435 appearances and 280 goals later, unleashing him was one of Sherwood’s better moments.
His first game saw Spurs knocked out of the League Cup, before being handed the permanent role a few days later. Unfortunately, losses to Arsenal (twice) combined with heavy defeats to Liverpool and Manchester City during his spell meant he only lasted until the end of the 2013/14 season.
His replacement was Pochettino, who enjoyed a much more productive time in charge of the club.
2 José Mourinho November 2019 – April 2021
Following the surprise sacking of Mauricio Pochettino, it was evident that Spurs would need a manager who could take the club to the next level – winning trophies.
On that note, José Mourinho sounded like the ideal candidate. His most recent spell at Manchester United had seen him win two major trophies in his debut season, although things soon turned sour.
The Portuguese manager lasted just 86 games in charge, leading the club to a sixth-place finish in the 2019/20 campaign. Indeed, it was Mourinho who last led the club to a major final, securing their place in the League Cup finale against Manchester City.
By the time the game rolled around, the former Chelsea boss had been sacked, lasting just 17 months in north London. Given the promise his appointment had, Mourinho’s time at Spurs was hugely underwhelming.
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ByRoss Kilvington 1 Nuno Espírito Santo July 2021 – November 2021
It is perhaps no surprise to see Nuno Espírito Santo ranked as the worst manager the club have had since 2008, as his spell at the club was nothing short of dismal.
He did work wonders with Wolverhampton Wanderers, guiding them from the Championship to consecutive seventh-place finishes in the top flight, but at Spurs, he struggled majorly.
Overall, he managed the club for just 17 games, winning nine, but the football on show was largely forgettable. Losses to Arsenal, Manchester United, Chelsea and Crystal Palace in the top flight didn’t exactly help his cause and he was sacked in November 2021.