Before his career ended completely with a low-key stint at Peter Reid's second-tier Coventry City in 2004 (Sherwood only made 11 appearances for the club due to persistent injury), Tim Sherwood's Premier League career was abruptly brought to halt in a match against none other than Tottenham Hotspur. In a match at Pompey's Fratton Park on the 26th of December in 2003, whilst playing for Portsmouth, Sherwood broke his leg against the team he now manages and this would be the last time he played for the club and the moment which would ultimately lead to his retirement, as he never fully recovered from it. In the 77th minute of the game, Spurs' Argentinian full-back Mauricio Taricco went in hard on Sherwood and he was taken off on a stretcher with X-rays later revealing a double fracture of his leg.
