2005/06 season - Mamelodi Sundowns edged out Orlando Pirates and Kaizer Chiefs in the 2005/06 Castle Premiership title race.

2004/05 season - Orlando Pirates led the title race for a large portion of the season, only for Kaizer Chiefs to stage a late Collins Mbesuma-inspired comeback to successfully defend their league crown.

2003/04 season - Kaizer Chiefs pipped Ajax Cape Town to the post to win their first league title in 11 seasons.

2002/03 season - Orlando Pirates, boosted by the goals of the late Lesley Manyathela, ran away with the Castle Premiership title, while Bush Bucks and African Wanderers succumbed to relegation.

2001/02 season - Santos were somewhat surprisingly crowned champions, giving coach Gordon Igesund his third Castle Premiership title with three different clubs, while AmaZulu and Tembisa Classic were relegated.

2000/01 season - Orlando Pirates were crowned Castle Premiership champions in 2001 as Kaizer Chiefs once again had to settle for second. Bloemfontein Celtic and African Wanderers were relegated.

1999/00 season - Mamelodi Sundowns made it three Castle Premiership championships in a row, topping the table in 2000 and running away from Orlando Pirates. At the other end AmaZulu and Mother City were relegated.

1998/99 season - Mamelodi Sundowns took the Castle Premiership title on goal difference from Kaizer Chiefs, while Dynamos and Vaal Professionals were relegated.

1997/98 season - Mamelodi Sundowns were the Castle Premiership champions of 1998 as African Wanderers and Real Real Rovers were relegated.

1996/97 season - Manning Rangers were crowned champions in the first Castle Premiership season with Warriors and Witbank Aces taking the drop.