Tottenham Hotspur have seen five permanent managers come and go since 2011, so how do the generals compare?
Harry Redknapp, Andre Villas-Boas, Tim Sherwood, Mauricio Pochettino and Jose Mourinho have all led Tottenham for different durations and to various degrees of success in the last decade.
Here’s each manager’s report card from their time in charge at Tottenham Hotspur. They’re ranked with grades in order of performance.

5. Tim Sherwood — 2013-2014
Tim Sherwood was barely in charge long enough to get his name inscribed on the manager’s door at White Hart Lane. He took over from André Villas-Boas in December of 2013 and remained in charge until the end of that Premier League season.
Sherwood lost his first game as Spurs’ manager in the League Cup, falling 2-1 to West Ham in the fifth round of the competition. The manager-turned-pundit has a lot to say about how the club is currently being ran, a lot of which rings true. He’s definitely more influential in the broadcast booth than he was on the touchline.
Tottenham finished sixth in the Premier League under Sherwood’s short rein. The Englishman, who also played for the north London club for four years, won 14 of his 28 matches as gaffer. He was undoubtedly one of the most passionate managers in the last decade. The 52-year-old wears his heart on his sleeve, but was more of a man manager, a galvanizer, than he was a tactician.
Spurs were also ousted in the FA Cup early under his tutelage, with the club losing in the third round of that competition. A short-lived rein in his dream position, Sherwood was replaced at the end of the season by Mauricio Pochettino.
Overall Grade — D

4. Jose Mourinho — 2019 – 2021
The Special One moved into Mauricio Pochettino’s former office with 24 hours of the Argentine’s dismissal. Keen to get cracking on his new appointment, Jose was appointed to bring a trophy to the north London club for the first time in 13 season.
His rein started extremely well, like most of his tenures do. He got most players to buy in to his dogmatic system, one that demands unerring discipline and organization. Those who weren’t onboard with his approach quickly found themselves on the outside looking in. But as long as the results were trending in the right direction, which they were, alienating a few players was tolerated, mere collateral damage from his my-way-or-the-highway motif.
Jose took a reeling Tottenham side, who were in 14th place at the time of Pochettino’s dismissal, to an eventual sixth place finish. The initial trajectory after his exquisite start had Tottenham pushing for a Champions League spot. Unfortunately injuries started to mount and Jose’s early inspirational effect on the squad began deteriorating.
After digging Tottenham out of a deep early season hole, Tottenham’s sixth place finish with Jose at the helm is still seen as a veritable achievement. Jose endured a rash of injuries that would paralyze any team.
The unprecedented season was halted due to a surging Covid-19, which ironically, in football terms, benefitted Spurs. It allowed the club’s top players — including Harry Kane and Son Heung-min — to recover from their respective ailments in time to make a charge for qualification into the Europa League. Prior to the extended break in play, Tottenham were ousted convincingly by Leipzig in the Champions League Round of 16.
A near immaculate start — highlighted by thrashing Manchester United 6-1 at Old Trafford — to the current campaign provided Spurs fans with real hope. But the wheels flew off violently, as they so often do during Mourinho’s tenure at a club. He lost the locker room and subsequently, just six days shy of the Carabao Cup Final, got axed ruthlessly by Daniel Levy.
Jose ran the touchline for 86 matches, winning 44. That’s a 51 percent winning rate.
Overall Grade — C

3. André Villas-Boas – 2012-2013
Some people will think that Villas-Boas and Mourinho should switch places at numbers three and four.
Another Portuguese manager, Villas-Boas resembled uncannily Mourinho’s path to managerial superstardom. The young prodigy in 2011 became the youngest manager, 33 years and 213 days, to win a European competition. His Porto defeated fellow Portuguese side Braga 1-0 in the Europa League Final.
The charismatic gaffer took the lead at Spurs after being dismissed by Chelsea. Villa Boas to this day has the highest winning percentage of any Spurs manager in the Premier League era. He won 44 of his 80 matches in charge, a 55 percent winning rate. While winning 55 percent of matches is no easy feat, Villas-Boas’ sample size is comparatively small, lessening the impact of the achievement.
He didn’t last two full seasons in charge; the Portuguese was relieved of his duties in December 2013, just a few months into his second season as Tottenham gaffer.
Villas-Boas’ Spurs beat Manchester United for the first time in 23 years at Old Trafford, a profound moment in club history.
Even though Tottenham finished a point adrift of fourth place and an all-coveted Champions Leagues spot, they set a new club record by amassing 72 points. At the time, it was the highest points tally ever achieved by any club in the Premier League not to finish in the top four.
Tottenham also qualified for the Europa League quarterfinal after an epic comeback victory in the Round of 16 against Inter Milan. Spurs lost in the quarterfinal to Basel.
Overall Grade B-

2. Harry Redknapp 2008-2012
At number two, Harry Redknapp is both an emotional and analytical choice. The don of gaffers enjoyed a comparatively long and fruitful tenure as Tottenham gaffer. For this piece, I’m more interested in his last year in charge, as that falls within the 10-year timeframe.
His last season as gaffer – 2011-2012 – Tottenham finished in fourth place, meaning a Champions League berth for the subsequent campaign. That was no easy feat for a side that Redknapp improved significantly during his time in north London.
Redknapp, after taking over from the outgoing Juande Ramos in 2008, led Spurs to a middling eighth place finish in the league. He then revolutionized Tottenham, taking them to perennial Champions League challengers. He led Tottenham to two fourth place and a fifth place finish in his last three years at the helm.
He won 98 of his 198 matches in charge, a 49 percent winning ratio. He also led Tottenham to an FA Cup semifinal in which Spurs lost 5-1 to Chelsea.
Overall Grade B

1. Mauricio Pochettino 2014-2019
Mauricio Pochettino is unequivocally Tottenham’s best manager from the last decade, if not the best ever. With an unbridled devotion to providing youth with a chance to flourish, Pochettino nourished and developed the likes of Harry Kane, Dele Alli, Christian Eriksen, to name just a few.
He was appointed manager on May 27, 2014. Less than a year later, Tottenham made it to the League Cup Final where they lost 2-0 to Chelsea. It was the first cup final Tottenham had appeared in since winning the League Cup in 2008.
Tottenham qualified for the Champions League in all but one of his five seasons in charge. His first campaign saw Spurs finish fifth in the Premier League. Tottenham finished in 3rd, 2nd, 3rd and fourth in the four subsequent seasons under his guidance. He also led Spurs to two successive FA Cup semifinals — in 2016/17 and 2017/18 — and a League Cup semifinal in the following season, 2018/19.
Of course his primary claim to fame is taking an injury-riddled Spurs side to the 2018-19 Champions League Final. Coming back to defeat Ajax in the semifinal thanks to Lucas Moura’s last-minute heroics will go down as one of the most epic moments in club history.
Pochettino was renowned for implementing an incredibly high energy press, which garnered almost immediate results. He elicited the best from his young side and will go down as one of Tottenham’s best managers of all time.
The messiah won 159 of his 293 matches at the helm, a 54 percent winning rate. That’s only one percent lower than Villas-Boas in a much larger sample size.
The only knock on his CV is falling at the last hurdle numerous times. For all his greatness, Pochettino was never able to win an elusive trophy, a regrettable blemish on an otherwise immaculate CV.
Wish he would take the current opening.

