Started his career with his local side, Watford before moving on to Norwich City after only 32 first team appearances. Established a reputation there when the side was in the top flight, but was tempted away by Kenny Dalglish to be part of the Blackburn revival, which ended with him lifting the Premiership trophy in 1995. Won his first England caps after his move to White Hart Lane and was unlucky not to win something in his first season when Spurs lost to Newcastle in the FA Cup semi. Sherwood added another option in midfield for George Graham and his Premiership experience was a useful addition to the squad, especially with a UEFA Cup campaign due in 1999-2000.
A driving force in midfield and with an ability to keep the ball moving through the midfield, the 1999-2000 season's campaign for him ended early with abdominal surgery for an injury he had been carrying for a long time. Fell out of contention for a place in England's Euro 2000 squad and has did not return to his best form in 2000-2001, as his passing has been less than his usual best and he appears to have slowed visibly. Took the captain's armband, but this gave him a licence to point and it was only in the last two games that he displayed some leadership.
Pre-season 2001-2002 saw the newspapers link the midfielder with moves to Wolverhampton Wanderers, Everton, Aston Villa, West Ham United, Watford, Blackburn and Southampton. The purchase of Poyet was seen as a straight replacement for him, but he was still at Spurs and came in as the holding midfielder when Freund picked up a cruciate injury at Chelsea in the first leg of the Worthington Cup semi-final. Scored in the return game, but didn't shine in the final and for the remainder of the season seemed to be going backwards.
At the start of the 2002-03 season, his criticism of Hoddle and the board in a Sunday newspaper seemed to have signalled the end of his time at White Hart Lane, but buyers were concerned about his wage demands.
After criticising Glenn Hoddle in a newspaper article prior to season 2002-03, he was effectively shut out of first team action, along with injuries that prevented him playing for the reserves. It was no surprise that he moved on to Portsmouth in the January 2003 transfer window, helping them gain promotion to the Premiership.
Had a short spell with Coventry City in 2004 before retiring from the game that end of the season and has been acting as an agent, working in conjunction with Jamie Redknapp on a lifestyle magazine for footballers and also is a pundit on Setanta Sports.