Fortune was signed by former United manager Sir Alex Ferguson for a fee of £1.5 million some 18 years ago, but got his first taste of European football at Premier League rival.
Before his time in Manchester, Fortune moved from Cape Town to England to play for Tottenham Hotspurs at junior level. However, due to work permit issues, he then relocated to Spain where he played for Mallorca in 1995.
A year later, he made the switch to Atletico Madrid, where his performances for the Atletico B team caught the attentions of Sir Alex, who subsequently swooped for the midfielder.
The Capetonian spent seven years with the Old Trafford side, making 126 appearances and scoring 11 times in all competitions. Fortune also won a number of trophies whilst in a United shirt, including the Premier League title, FA Cup, Intercontinental Cup and Club World Cup.
In 2006, he departed Old Trafford on a free transfer to join Blackburn Rovers.
Eighteen years after his debut for United, 40-year-old Fortune is retired from playing but is still involved in football, occasionally giving his expert opinion in interviews for MUTV.
Fortune has also been constantly tipped as a future Bafana Bafana coach. Whatever the case, he has surely come a long way since 1999.