| 20 May 2025
PSL Premiership |
 Supersport United |
0–1 |
 Orlando Pirates |
W |
| 8 Mar 2025
Nedbank Cup · Quarter-finals |
Supersport United |
2–2 (aet, 4–5 pens) |
Orlando Pirates |
D |
| 22 Oct 2024
PSL Premiership |
Orlando Pirates |
2–0 |
Supersport United |
W |
| 3 Aug 2024
MTN8 · Quarter-finals |
Orlando Pirates |
3–1 (aet) |
Supersport United |
W |
| 25 May 2024
PSL Premiership |
Orlando Pirates |
1–1 |
Supersport United |
D |
| 23 Dec 2023
PSL Premiership |
Supersport United |
3–1 |
Orlando Pirates |
L |
| 18 Mar 2023
PSL Premiership |
Orlando Pirates |
1–0 |
Supersport United |
W |
| 21 Aug 2022
PSL Premiership |
Supersport United |
0–0 |
Orlando Pirates |
D |
| 30 May 2022
PSL Premiership |
Supersport United |
2–0 |
Orlando Pirates |
L |
| 16 Mar 2022
PSL Premiership |
Orlando Pirates |
3–2 |
Supersport United |
W |
| 24 Feb 2021
PSL Premiership |
Supersport United |
1–1 |
Orlando Pirates |
D |
| 21 Nov 2020
PSL Premiership |
Orlando Pirates |
2–1 |
Supersport United |
W |
| 29 Aug 2020
PSL Premiership |
Orlando Pirates |
2–1 |
Supersport United |
W |
| 14 Aug 2019
PSL Premiership |
Supersport United |
3–0 |
Orlando Pirates |
L |
| 20 Feb 2019
PSL Premiership |
Supersport United |
1–0 |
Orlando Pirates |
L |
| 15 Sep 2018
PSL Premiership |
Orlando Pirates |
3–1 |
Supersport United |
W |
| 11 Apr 2018
PSL Premiership |
Supersport United |
0–0 |
Orlando Pirates |
D |
| 5 Dec 2017
PSL Premiership |
Orlando Pirates |
0–0 |
Supersport United |
D |
| 7 Mar 2017
PSL Premiership |
Orlando Pirates |
1–1 |
Supersport United |
D |
| 1 Nov 2016
PSL Premiership |
Supersport United |
6–1 |
Orlando Pirates |
L |