Fortune began his professional football career with
Tottenham Hotspur. In 1995, he moved to Spain to play for
Mallorca, but soon moved on to
Atlético Madrid, where he mostly played for the
B team. In August 1999, Fortune had a trial at
Manchester United, prompting manager
Alex Ferguson to sign him for a fee of £1.5 million; Fortune turned down a move to
Real Valladolid to secure the move to Manchester United. He made his first appearance for the club against
Newcastle United on 30 August. His first goal followed on Boxing Day 1999 against
Bradford City, and he scored twice against
South Melbourne in the
2000 FIFA Club World Championship. Despite playing in three
Premier League winning seasons (
1999–2000,
2000–01 and
2002–03), Fortune never played the required 10 games stipulated to earn a winner's medal. However, he was awarded a Premier League winner's medal by special dispensation following United's title success in 2003 during which he had appeared nine times in the league that season. It is commonly incorrectly reported that this medal had been left at the club by a former player. After being used mostly in a squad rotation basis for his career at Manchester United, he was released by the club ahead of the
2006–07 campaign. After a successful trial, Fortune joined
Bolton Wanderers for the 2006–07 season. In September 2008, he joined
Sheffield United on trial. On 6 October 2008,
Serie B club
Brescia confirmed to have reached an agreement with Fortune; the transfer was finalised on 23 October, with Fortune signing a one-year contract with the
Rondinelle. On 2 February 2009,
Tubize signed Fortune on a free transfer. On 4 August 2009, he signed a short-term deal at
Doncaster Rovers. He scored his first Rovers goal against
Ipswich Town on 19 September 2009. He was sent off in a 2–2 draw against
Scunthorpe United. Fortune was not offered an extension to his deal at the club and was released on 4 February 2010. ==International career==