[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 |
Home History
| South Africa Premier | 2023/12/23 15:45 | Supersport United v Orlando Pirates | L | 3-1 |
| South Africa Premier | 2023/12/17 13:30 | Golden Arrows v Orlando Pirates | W | 1-2 |
| South Africa Premier | 2023/12/09 18:00 | Orlando Pirates v TS Galaxy | W | 1-0 |
| South Africa Premier | 2023/12/05 17:30 | Orlando Pirates v Moroka Swallows | W | 2-0 |
| South Africa Premier | 2023/11/25 13:30 | Richards Bay FC v Orlando Pirates | D | 0-0 |
| South Africa Premier | 2023/11/11 13:30 | Kaizer Chiefs v Orlando Pirates | W | 0-1 |
| South Africa Premier | 2023/11/07 17:30 | Orlando Pirates v Sekhukhune United FC | W | 1-0 |
| South Africa Cup | 2023/11/04 13:00 | Richards Bay FC v Orlando Pirates | L | 5-4 |
Away History
| South Africa League Cup | 2023/12/16 13:00 | Stellenbosch FC v TS Galaxy | W | 6-5 |
| South Africa Premier | 2023/12/08 17:30 | Stellenbosch FC v Cape Town City | W | 1-0 |
| South Africa Cup | 2023/12/02 13:00 | Richards Bay FC v Stellenbosch FC | W | 0-3 |
| South Africa Premier | 2023/11/28 17:30 | Cape Town Spurs v Stellenbosch FC | W | 0-3 |
| South Africa Premier | 2023/11/25 13:30 | Amazulu v Stellenbosch FC | W | 0-1 |
| South Africa Premier | 2023/11/11 18:00 | Chippa United v Stellenbosch FC | D | 0-0 |
| South Africa Premier | 2023/11/07 17:30 | Stellenbosch FC v Richards Bay FC | W | 2-1 |
| South Africa Cup | 2023/11/03 17:30 | Polokwane City v Stellenbosch FC | W | 0-2 |
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