Every meeting

22 Feb 2025 PSL Premiership	Orlando Pirates	2–1	Cape Town City	L
8 Jan 2025 PSL Premiership	Cape Town City	1–0	Orlando Pirates	W
31 Aug 2024 MTN8 · Semi-finals	Orlando Pirates	2–0	Cape Town City	L
28 Aug 2024 MTN8 · Semi-finals	Cape Town City	1–1	Orlando Pirates	D
1 May 2024 PSL Premiership	Cape Town City	0–2	Orlando Pirates	L
29 Aug 2023 PSL Premiership	Orlando Pirates	2–0	Cape Town City	L
22 Apr 2023 PSL Premiership	Orlando Pirates	2–1	Cape Town City	L
7 Jan 2023 PSL Premiership	Cape Town City	2–1	Orlando Pirates	W
2 Mar 2022 PSL Premiership	Orlando Pirates	0–0	Cape Town City	D
2 Oct 2021 PSL Premiership	Cape Town City	1–1	Orlando Pirates	D
9 Feb 2021 PSL Premiership	Orlando Pirates	2–0	Cape Town City	L
5 Dec 2020 PSL Premiership	Cape Town City	2–2	Orlando Pirates	D
17 Oct 2020 MTN8 · Quarter-finals	Orlando Pirates	1–0	Cape Town City	L
23 Aug 2020 PSL Premiership	Cape Town City	1–0	Orlando Pirates	W
28 Sep 2019 PSL Premiership	Orlando Pirates	3–3	Cape Town City	D
4 May 2019 PSL Premiership	Cape Town City	2–2	Orlando Pirates	D
19 Sep 2018 PSL Premiership	Orlando Pirates	2–2	Cape Town City	D
28 Apr 2018 PSL Premiership	Cape Town City	1–0	Orlando Pirates	W
14 Mar 2018 Nedbank Cup · 8th Finals	Cape Town City	1–0	Orlando Pirates	W
19 Sep 2017 PSL Premiership	Orlando Pirates	1–0	Cape Town City	L
18 Feb 2017 PSL Premiership	Cape Town City	2–2	Orlando Pirates	D
20 Sep 2016 PSL Premiership	Orlando Pirates	0–0	Cape Town City	D

This record covers meetings from 20 September 2016 onwards. Earlier games between these teams aren't on the site yet, so the all-time totals may be higher.
W / D / L from Cape Town City's side. Penalty shootouts count as draws.