Teams Rupert Bailey played for
| Main FC | Boland (1998/99-2005/06) |
| Easterns (2001/02-2003/04) | |
| Main ListA | Northerns (2000/01) |
| Easterns (2001/02-2002/03) | |
| Boland (2004/05-2005/06) | |
| SuperSport Series | Easterns (2001/02-2003/04) |
| Miscellaneous | Boland Academy (1998/99) |
| Boland B (1999/00) | |
| Northerns B (2000/01) | |
| Northerns Academy (2000/01) | |
| Northerns Invitation XI (2000/01) | |
| Easterns (2002/03) | |
| Boland (2004/05) |
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