Upon signing he immediately became a regular in the side that went on to win the First Division Championship that season, scoring once in the process, in a 5–0 win away to Millwall on 1 March. Sherwood remained an important member of the Pompey squad for the first half of the 2003–04 Premier League season, scoring a brace in a 5–2 win against Third Division Northampton Town in the League Cup second round on 23 September. He broke his leg against Tottenham on 26 December, after a challenge by his former teammate Taricco. It was to be his last match for the club as, along with fellow veteran Teddy Sheringham, he was released in the 2004 close season. Coventry City On 9 July 2004, Sherwood signed for Peter Reid's Coventry City on a two-year deal with Coventry and said that he would "desperately like to achieve promotion" with the club. 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 end of the 2004–05 season, Coventry had not been promoted and the club announced that Sherwood could leave on a free transfer. He parted company with the Sky Blues by mutual consent on 1 July 2005. International career During his time with Blackburn Rovers he added an England B cap to the England Under 21 honours he picked up whilst at Norwich. 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. He earned a further two caps that year: in a 1–1 friendly draw with Hungary in Budapest on 28 April, and a goalless qualifying draw with Sweden at Wembley on 5 June. Managerial career Tottenham Hotspur In October 2008, Sherwood joined Tottenham Hotspur as assistant first team coach, under new manager Harry Redknapp. Sherwood became Technical Director in 2012 and in that role led Spurs' Under-21 side in the inaugural Under-21 Premier League season, guiding the side to finish top in both group and elite stages. Sherwood's side eventually lost the league final 3–2 to Manchester United. On 16 December 2013, Tottenham announced that Sherwood would "assume first team coaching duties" following the departure of André Villas-Boas as the manager. He lost his first game in charge, 2–1