[4] Orlando Pirates 2-3 Stellenbosch FC [5] 2023-12-29 18:00
Stadium: Orlando Stadium Round: 16
Referee: Abongile Tom Home Manager: Jose Riveiro Away Manager: Steve Barker
Head to Head
| South Africa Supa 8 Cup | 2023/09/24 13:00 | Orlando Pirates v Stellenbosch FC | L | 0-1 |
| South Africa Supa 8 Cup | 2023/09/03 13:00 | Stellenbosch FC v Orlando Pirates | W | 1-2 |
| South Africa Premier | 2023/08/05 18:00 | Stellenbosch FC v Orlando Pirates | L | 1-0 |
| South Africa Premier | 2023/01/22 13:30 | Orlando Pirates v Stellenbosch FC | W | 4-1 |
| South Africa Premier | 2022/08/10 17:30 | Stellenbosch FC v Orlando Pirates | D | 1-1 |
| South Africa Premier | 2021/11/24 15:30 | Stellenbosch FC v Orlando Pirates | W | 0-3 |
| South Africa Premier | 2021/08/21 13:00 | Orlando Pirates v Stellenbosch FC | D | 2-2 |
| South Africa Premier | 2021/05/11 13:00 | Stellenbosch FC v Orlando Pirates | D | 0-0 |
| South Africa Premier | 2020/10/28 17:30 | Orlando Pirates v Stellenbosch FC | D | 1-1 |
| South Africa Premier | 2020/09/05 13:30 | Orlando Pirates v Stellenbosch FC | W | 1-0 |
| South Africa Premier | 2019/10/26 13:30 | Stellenbosch FC v Orlando Pirates | L | 1-0 |
| South Africa League Cup | 2019/10/19 16:00 | Orlando Pirates v Stellenbosch FC | W | 1-0 |