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.