The most contested accolade to come out of the PSL is the player of the season. Every player playing in the PSL has hopes at the beginning of the season to be the last PSL man standing. These are the 5 players who have taken the accolade in the last 5 seasons of the PSL.
- Thulani Serero, who now plays overseas for Ajax Amsterdam took the player of the season for the 2011/2012 season while playing for Ajax Cape Tow. The Soweto born magician kept opponents awake and stressed each time they had to face Ajax Cape Town.
- Dubbed South Africa’s finest, Itumeleng Khune, took the player of the season in the 2012/2013 season by keeping a clean sheet for Chiefs in 19 games unbeaten.
- Sibusiso Vilakazi, took player of the season in 2013/14 season while playing for his former side Bidvest Wits F.C. Vila is now playing for Sundowns and is scoring goals.
- Then a defender came and took the accolade, that is none other than, Tefo Mashamaite, who then left Chiefs and went to play overseas following in the footsteps of Thulani Serero.
- 2015/16 season was dominated by none other than Khama Billiat who plays for Mamelodi Sundowns. After missing much of the 2014/15 season because of injury, Billiat came back in 2015/16 and took the play of the season.