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.

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.

[4] Sherwood won a runners-up medal with Spurs in the 2002 League Cup Final, when they were beaten by his former club Blackburn.

[9] Although he was the captain, he was unpopular with fans, due to his frequent injuries, high wages and decision to do television punditry during his spell.

At the age of 30, Sherwood made his debut for England in their 3–1 UEFA Euro 2000 qualification victory over Poland at Wembley on 27 March 1999, under new manager Kevin Keegan.

[12] In October 2008, Sherwood joined Tottenham Hotspur as assistant first team coach, under new manager Harry Redknapp.

[14][15] On 16 December 2013, Tottenham announced that Sherwood would "assume first team coaching duties"[16] following the departure of André Villas-Boas as the manager.

Tim Sherwood was best known for being on the receiving end of Jorge Jesus' famous touchline dance, when he held up 3 fingers to indicate that Benfica had just scored 3 goals during their Europa League tie in 2014.

[25][26] Sherwood led Villa to Wembley for the first time since 2010 just four days later, after winning 2–0 in the FA cup quarter-final again against West Bromwich Albion.

[29] On 19 April 2015, Aston Villa reached the FA Cup Final for the first time since 2000, coming from behind to defeat Liverpool 2–1 in their semi-final at Wembley.

[31] After losing six consecutive matches, including a nine-game winless run which left the team 19th in the table, Sherwood was sacked on 25 October 2015.