1. PITSO MOSIMANE: Five Titles
- 2013/14
- 2015/16
- 2017/18
- 2018/19
- 2019/20 (All Mamelodi Sundowns)
2. GAVIN HUNT: Four Titles
- 2007/08( SuperSport United)
- 2008/09 (SuperSport United)
- 2009/10 (SuperSport United)
- 2016/17 (Bidvest Wits)
3. GORDON IGESUND: Four Titles
- 1996/97 (Manning Rangers)
- 2000/01 (Orlando Pirates)
- 2001/02 (Santos)
- 2006/07 (Mamelodi Sundowns)
4. TED DUMITRU: Four Titles
- 1997/98 (Mamelodi Sundowns)
- 1998/99 (Mamelodi Sundowns)
- 2003/04 (Kaizer Chiefs)
- 2004/05 (Kaizer Chiefs)
5. STUART BAXTER: Two Titles
- 2012/13 (Kaizer Chiefs)
- 2014/15 (Kaizer Chiefs)