He soon broke into the first team, initially playing out of position at left back before replacing Ralph Milne as left-winger in the 1990–91 season. He played a key part in United's success in the European Cup Winners' Cup that season scoring a hat-trick against Arsenal at Highbury in the 1990 League Cup. United eventually won the game 6–2. Sharpe himself, cites this as one of the best memories in his footballing career.
Having established himself as a left winger, Sharpe earned a call up to the England squad, although he was unable to replace John Barnes as first choice left winger. Unfortunately, he was then out of the game for long periods of time through injury and illness (he suffered from viral meningitis) and when his fitness recovered the form of Ryan Giggs meant he had to play out of position at left back or on the right wing, competing for a place with Andrei Kanchelskis. In total he played 265 games for the Red Devils during eight years there, scoring 36 goals.
Despite his injury history, Leeds United signed him for £4.5 million in the summer of 1996, making him their record signing. Again his time at Leeds was beset by further injuries. He made 26 Premiership appearances in 1996–97, scoring five goals, but a pre-season knee injury ruled him out for the entire 1997–98 season and he was unable to regain his place in the team on recovery.
In the autumn of 1998, he was loaned to Italian Serie A strugglers Sampdoria, but soon fell out of favour and in the New Year he returned to England. He signed on loan for Bradford City in March 1999 and he helped in securing the club's promotion to the Premiership after 77 years outside the top division. He joined Bradford in a £250,000 deal during the summer and helped preserve the club's Premiership status in 1999–00.
In 2000–01, Sharpe lost his place in the Bradford team and just before Christmas went on loan to Division One Portsmouth. He returned to Bradford during the 2001–02 season but when his contract expired at the end of the season he was given a free transfer. Following a brief trial stay with Grimsby Town he signed for Exeter City before he moved to Grindavík in Iceland. In June 2003 he announced his retirement from professional football at the age of 32.
During 2003–04, Sharpe made a brief return to football in the Kidderminster Sunday League with Hoobrook Crown before signing for Northern Counties East Premier League side Garforth Town the following summer.
Sharpe has emerged as a key member of The England Legends, a squad of former internationals who play one-off games against counterparts from Italy, Germany, Ireland and Scotland.
Sharpe has also developed a career in reality television. He appeared as a competitor in the 2005, ITV television show Celebrity Wrestling, under the name "Sharpe Shooter." He is best known though for appearing in Celebrity Love Island. During his time on the Island Sharpe courted the attentions of many of the show's ladies, most notably TV presenter Jayne Middlemiss, who confessed to "never having felt like this before about someone," but Sharpe eventually dated Abi Titmuss.
In 2007 Sharpe appeared as a contestant in ITV's Dancing On Ice. He was eliminated from the competition on 3 March 2007. He was to also appear in ITV's popular TV soap Coronation Street as an extra in the fictional pub "The Rovers Return" as a working class taxi driver from Manchester.
In November 2005 Sharpe visited York to attend a graduation ceremony at the Minster. He later dined in the popular VJ's Art Bar which has become affectionately known to locals as 'The Lee Sharpe Bar'.
Sharpe, alongside former Bucks Fizz singer Cheryl Baker, currently fronts a London Underground advertising campaign for Nourkrin, a baldness treatment. He is billed as "Of Celebrity Love Island fame!"
He has recently starred in Dec's team on Ant V's Dec, on Saturday Night Takeaway ITV1.
Appeared in the 2008 television series Superstars on Channel Five.
After he dated other women, Sharpe and Titmuss split up, but by February 2007 he was back with Petty.
Sharpe is now an after dinner speaker.