As a player, he was a midfielder from 1987 until 2005, notably as captain of Blackburn Rovers' Premier League title-winning side in 1995. He also played for Watford, Norwich City, Tottenham Hotspur, Portsmouth and Coventry City. He made three appearances for the England national team in 1999.
Sherwood began his coaching career at Tottenham Hotspur, progressing from assistant first team coach to manager in a five-year spell, then managing the club from December 2013 to his dismissal in May 2014. He resumed his managerial career at Aston Villa in February 2015, taking them to that season's FA Cup final and saving them from relegation from the Premier League, until being sacked in October 2015. In November 2016, Sherwood was appointed as director of football at Swindon Town.
Born in Borehamwood, Hertfordshire, Sherwood supported Arsenal as a child. He made his debut for Watford against Sheffield Wednesday on 12 September 1987. He made a total of 32 league appearances in Division Two for Watford before moving to Norwich City in July 1989. He played 88 games scoring 13 goals for Norwich before joining Blackburn Rovers in February 1992.
As one of Kenny Dalglish's first signings for Blackburn, he initially struggled to make the first team but went on to become a core player. Under his captaincy, Blackburn finished second in the Premiership in 1993–94 before winning it the following season. During his time at the club Dalglish wanted to sign both Zinedine Zidane and Christophe Dugarry, who were playing in France for Bordeaux, but Rovers owner Jack Walker reportedly said to Dalglish: "Why do you want to sign Zidane when we have Tim Sherwood?"
With Sherwood unsettled in 1999 and having family and business links in Hertfordshire, George Graham paid a reported fee of £3 million to bring him to Tottenham Hotspur in the first week of February 1999. He made his debut for Spurs as an 87th-minute substitute for Mauricio Taricco in the 0–0 draw with Coventry on 6 February. He was cup-tied for their victory in the 1999 Football League Cup Final. Sherwood won a runners-up medal with Spurs in the 2002 League Cup Final, when they were beaten by his former club Blackburn.