Since leaving Norwich for £325,000, Tim Sherwood has gained a Premiership Champions medal with Blackburn Rovers, £4million transfers and England honours

St Albans born Tim began his career with Watford. He made his debut against Sheffield Wednesday on the 12th September 1987. 31 more league appearances followed in Division Two. It was a surprise when Norwich paid £325,000 for him in July 1989. Obviously then City manager Dave Stringer recognised qualities within Tim that could be developed at Carrow Road. Stringer had missed out once before as Tim had been a schoolboy with Norwich but rejected a Carrow Road apprenticeship. Primarily a central midfielder, replacing Andy Townsend, Tim was able to play in the defence and on the right. After failing to turn up for a pre-season friendly against Romanian side Otelul Galati, he was fined and suspended. Future opportunities to add to his City appearances and goals were limited. He had a total of 88 games and 13 goals in Norwich colours 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 became an integral part of Dalglish's big spending Rovers side. Under Tim's captaincy, Blackburn finished second in the Premiership in 1993/94 before winning it the following season. Surprisingly he has not gained international recognition, adding only an England B cap to the England Under 21 honours he picked up whilst at Norwich.

Sherwood's relationship with Tottenham began in The Daily Mirror in the Summer of 1999 when it reported Tim was hoping to return to London as he has a home in St Albans. Tottenham are believed to have made initial bids but Blackburn would only accept £5million for the loss of their captain and midfield general. Blackburn manager Roy Hodgson dropped Sherwood for the clash at Spurs on 9th September saying "I only want players who are totally committed". Sherwood reacted angrily to this suggestion stating "It is hurtful and insulting. Anyone who knows me will tell you that I am a winner and that I always give 100%. I'm definitely not unsettled by all the speculation. I'm not a kid". The Evening Standard later revealed that Spurs made an initial bid of £2.9million and then upped it to £4million. It is unfortunate for Tim that this has happened at this moment in his career with an expected call-up to the England squad for the clash with Bulgaria. Tim has returned to the Blackburn line-up but his agent Eric Hall expected Spurs to make another £5million bid.

George Graham's appointment at Spurs as their new manager has put any move on hiatus as he gave the current squad a month to prove themselves (this could result in transfers for Ruel Fox and Neale Fenn). Tim though spoke out at Blackburn's refusal to discuss a transfer for Sherwood. He implied that as many internationals have left Ewood Park in recent months, the club lacks ambition and that Blackburn should treat him with the same respect and allow him to consider offers from other clubs. The Sunday People reported on 11th October that French giants Marseille were interested in signing Sherwood. After his sending off at Old Trafford against Manchester United on 14th November, Blackburn manager Roy Hodgson launched a vitriolic attack on Tim's professionalism suggesting that his patience with Tim was running out and that Sherwood could be the first casualty on this season's Ewood Park crisis. The Daily Mirror again reported on Tuesday 17th November that Tottenham would seek to bring both Sherwood and Chris Sutton to White Hart Lane. In January 1999, Tim's position at Blackburn again looked shaky as he rejected the club's final, improved offer of a new contract. Although he had three and a half years remaining on his contract and is prepared to see them out, Blackburn were tempted to reap their losses especially as new manager Brian Kidd splashed out of Irish international midfielder Jason McAteer from Liverpool. With Sherwood unsettled and having family and business links in Hertfordshire, Tottenham and Arsenal were the firm favourites for his signature, with George Graham again prepared to offer £4million for his services. This speculation came true in the first week of February 1999 as Sherwood joined Spurs supposedly for £3million. He made his debut as a 87th minute substitute for Tarrico in the 0-0 draw with Coventry on 6th February 1999.

Tim made an impressive debut at the age of 30 for England in their 3-1 victory over Poland at Wembley on 27th March 1999, his debut being handed to him by new England manager Kevin Keegan. In the autumn of 2000, Tim was surprisingly linked by the media with a move back to Vicarage Road whilst January 2001 saw a return to Ewood Park mooted in the media. Supposedly Blackburn made a £3million bid to re-sign Tim following Dennis Wise's rejection of a move from Chelsea to Blackburn.

The summer of 2001 was filled with rumours regarding Tim's future. June 2001 saw Tim linked with a £3million to Wolves whilst Aston Villa were also linked with rumours suggesting an exchange for David Ginola. However it appears from Evening Standard on 8th June 2001 that Tim will be offered a new contract and the club captaincy in order to keep him at White Hart Lane. Allegedly Hoddle wants to build his new look Tottenham around Tim! July 2001 saw the media speculate regularly that Sherwood would be departing from Tottenham. On the 15th, he was linked with a £2million move to Southampton. A similar fee was suggested on the 22nd with a move to Everton. On the 29th, Tim was linked with moves to West Ham and Wolves. On August 19th, the News of the World speculated that Coventry were lining up a £3million swoop for Sherwood seeing him as the man to lead them back into the Premiership. At the end of August, Tim was linked with a move to Manchester City where he would team up again with his former England boss Kevin Keegan. On 14th October 2001, Charlton were added as a possible destination for Sherwood according to the Sunday Mirror.

Transfer speculation continued into the new year with January 2002 seeing Tim linked with a move to Scottish giants Rangers, possibly as part of a deal that would bring Tore Andre Flo to White Hart Lane. A switch to Ibrox arose again in March 2002 when Sherwood and Leonhardsen were said to be moving to Scotland in exchange for Rangers' Barry Ferguson. In May 2002, he was linked with a move to Aston Villa. Tim fell further out of favour at White Hart Lane in July 2002 receiving a fine of two weeks pay after criticising the club for a lack of ambition. However he helped restore himself with the winner in a pre-season friendly at Watford on 3rd August but the same weekend saw suggestions that Southampton would swoop for the former England midfielder. On 15th August the media suggested another move to the South Coast with Harry Redknapp's Portsmouth said to be preparing a £400,000 bid. The Pompey connection resurfaced in the middle of September 2002 with the media speculating that Tim would join the First Division leaders on loan, prior to a £250,000 move in January when the transfer window was lifted. Portsmouth manager Harry Redknapp confirmed his interest in Sherwood but was waiting for him to recover from injury.

Failure to be picked for Spurs' reserves in November 2002 indicated to the media that Sherwood's time at White Hart Lane was coming to an end. In addition to the Portsmouth rumours, Tim was also linked with Aston Villa and Watford. In January 2003, Tim leaked to the press that he had had a major argument with Spurs manager Glenn Hoddle and that Hoddle had told him that he would never play for the club again. Clubs said to be interested in this development included Portsmouth, Sunderland, Newcastle, West Bromwich Albion, Charlton and Bolton (possibly as part of a deal that would bring Michael Ricketts to White Hart Lane).

Throughout the January 2003 transfer window, Sherwood was linked with Portsmouth but it seemed as if this move would fall through when they could not agree a financial settlement. The media then reported his imminent signing for West Brom only for him to move to Portsmouth on a 4 month contract on January 29th 2003 - this deal was enabled by Spurs and Sherwood coming to a severance deal that suited both sides.

On April 11th 2004, the News of the World suggested that West Ham manager Alan Pardew was willing to offer Sherwood a two year deal if Portsmouth were relegated from the Premiership. Out of contract in June 2004, Sherwood has been offered a free transfer if Pompey are relegated. Even though Pompey survived the drop, Tim, and fellow veteran teammate Teddy Sherringham, were both released on May 14th 2004. The News of the World speculated on 6th June 2004 that Tim would be joining newly promoted QPR. In the end, he signed for Peter Reid's Coventry City on 9th July 2004 and vowed to win his third promotion to the Premiership. At the end of the 2004/5 season, Coventry announced that Tim could leave on a free transfer. He parted company with the Sky Blues by mutual consent on 1st July 2005.

In October 2005, media reports suggested that Sherwood was fronting a consortium to buy Spanish side Malaga.

In November 2008, Tim returned to Tottenham as a coach under the new management team of Harry Redknapp and Kevin Bond

At the end of September 2012, Tim was linked with the managerial vacacny at his former club Blackburn following the departure of Steve Kean.

When manager Andreas Villas-Boas was sacked by Spurs on 16th December 2013 following a 5-0 home defeat to Liverpool (following on from a 6-0 defeat to Man City two weeks previously), Sherwood was placed in charge as caretaker manager. He lost his first game in charge, 2–1 at home to West Ham in the fifth round of the Capital One Cup but four days later managed a 3–2 Premier League win over Southampton. On 23rd December 2013, Tottenham named Sherwood as their new head coach, handing him an 18-month contract until the end of the 2014–15 season.

After Spurs finished sixth, qualifiying for the Europa League, Sherwood was sacked on 13th May 2014 with Spurs activating a break clause in the contract. Despite hlding the highest win percentage in the Premier League for any Spurs manager, the Spurs board seem to want a more experienced manager with Dutchman Frank De Boer and Southampton's Mauricio Pochetitino linked with the vacancy. Sherwood was quickly linked with managerial vacancies at Norwich, Brighton and West Brom. In August 2014, Sherwood was strongly linked with the vacancy at Crystal Palace following Tony Pulis' resignation two days before the start of the 201415 Premier League campaign.

Over the Christmas 2014 / New Year period, he was linked with vacancies at West Brom (which went to Tony Pulis), Crystal Palace (Alan Pardew), Brighton (Chris Hughton), Newcastle and Norwich.

After Harry Redknapp resigned as QPR manager at the beginning of February 2015, Sherwood was quickly installed as the bookie's favourite for the position, with caretaker manager Chris Ramsay supporting Sherwood's candidacy.

Sherwood was appointed manager of Aston Villa on 14th February 2015 following the sacking of Paul Lambert on 11th February 2015. Appointments to his management team included Mark Robson and Tony Parks. He led Villa to safety from relegation and they also reached the FA Cup final only to lose 4-0 to Arsenal on 30th May 2015.

Sherwood was sacked as Villa's manager on 25th October 2015 with Villa at the bottom of the Premier League having lost six consecutive games. He had only managed the club for 28 games, the shortest reign in Villa's history.

In November 2016, Sherwood was linked with the vacancies at Wolves (finally filled by Paul Lambert) and at QPR following Jimmy Floyd Hasselbaink's sacking. In the end, he was appointed as Director of Football at League One side Swindon. he know Swindon chairman Lee Power from his time at Norwich and had lent the Robins Ryan Mason and Alex Pritchard whilst he was Spurs boss. The former Spurs manager was given responsibility for "transfers, the way we play, the formations and the picking of the team" - though head coach Luke Williams will remain in the role.

Despite an impressive 3-0 win over Charlton in their first game following Sherwood's arrival, the appointment did not result in a sustained improvement in form, as Swindon have won only seven of their 31 games since his hiring. At times, it was unclear whether or not Sherwood was managing the team, though in recent weeks his first-team responsibilities have decreased, and he has not attended all of the Robins' games.

Swindon were relegated into League Two on 22nd April 2017 following a 2-1 home defeat to Scunthorpe that left them in 22nd place. The club confirmed his departure on 14th June 2017. Swindon chairman Lee Power confirmed the club have changed their structure following the appointment of David Flitcroft as manager on 5 June. He then worked as a pundit.

At the start of April 2019, he was linked with the managerial vacancy at QPR following the sacking of Steve Maclaren after a 2-1 home defeat to lowly Bolton on Saturday 30th March, left them with just one win in 15 league games and 17th in the Championship table, eight points clear of the relegation zone. Sherwood is friends with former Tottenham team-mate Les Ferdinand, who is QPR’s director of football.