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The 1999–2000 South African Premiership, known as the 1999–2000 Castle Premiership for sponsorship purposes, and also commonly referred to as the PSL after the governing body, was the fourth season of the Premiership since its establishment in 1996. The season began on 30 July 1999 and ended on 4 June 2000. Mamelodi Sundowns once again managed to secure their crown, sealing their third successive PSL title. Along with their success in the PSL's predecessor - winning three National Soccer League titles in 1988, 1990 and 1993 - this gave Mamelodi Sundowns their 6th South African championship. Sundowns tallied 75 points for the season, equalling the points record they jointly set with Kaizer Chiefs last season, but unlike the previous season in which the title was decided by goal difference, there was no close title race this season as Sundowns finished comfortably ahead of second placed Orlando Pirates with an 11-point margin.
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