Fortune left South Africa for the United Kingdom at the age of 14 for Tottenham Hotspur but went on to make his professional breakthrough in Spain.
After spells with Real Mallorca and Atletico Madrid, the technically gifted midfielder was snapped up by Sir Alex Ferguson after United's iconic 1999 treble-winning season.
Now serving as the club's assistant coach for their U-23 side, he recalls how the move actually came about and concedes it came as a shock, even to his then teammates in Madrid.
"I was playing for Atletico Madrid when my agent told me he had been speaking to somebody at Manchester United and had arranged a trial," Fortune told Inside United.
"I couldn't believe it because United had won the Treble only two or three months before that, and I had watched United play against Bayern Munich in Barcelona in the 1999 Champions League final.
"I obviously wanted to play in England, but I thought the approach was a bit strange. I think my team-mates at Atletico thought it was strange, too! I went to Carrington in the summer of 1999 and the rest is history."
Fortune spent seven years at United scoring 10 goals and registering six assists in 126 games before injuries curtailed his career with the Premier League giants.