| Date | Match | League | Result | OU 2.5 | Both to score |
|---|---|---|---|---|---|
| 2/18/25 | Cape Town City vs Chippa United | Premier League | 0:2 | No | No |
| 12/14/24 | Chippa United vs Cape Town City | Premier League | 0:1 | No | No |
| 2/17/24 | Chippa United vs Cape Town City | Premier League | 1:1 | No | Yes |
| 11/7/23 | Cape Town City vs Chippa United | Premier League | 2:1 | Yes | Yes |
| 1/14/23 | Chippa United vs Cape Town City | Premier League | 1:1 | No | Yes |
| 10/25/22 | Cape Town City vs Chippa United | Premier League | 2:1 | Yes | Yes |
| 5/4/22 | Chippa United vs Cape Town City | Premier League | 0:0 | No | No |
| 11/3/21 | Cape Town City vs Chippa United | Premier League | 1:0 | No | No |
| 3/3/21 | Chippa United vs Cape Town City | Premier League | 0:0 | No | No |
| 2/28/21 | Chippa United vs Cape Town City | Nedbank Cup | 2:1 | Yes | Yes |
| 10/24/20 | Cape Town City vs Chippa United | Premier League | 1:1 | No | Yes |
| 8/14/20 | Chippa United vs Cape Town City | Premier League | 0:1 | No | No |
| 12/7/19 | Cape Town City vs Chippa United | Premier League | 0:1 | No | No |
| 4/26/19 | Chippa United vs Cape Town City | Premier League | 0:2 | No | No |
| 12/11/18 | Cape Town City vs Chippa United | Premier League | 1:1 | No | Yes |
| 3/2/18 | Cape Town City vs Chippa United | Premier League | 2:0 | No | No |
| 10/22/17 | Chippa United vs Cape Town City | Premier League | 2:1 | Yes | Yes |
| 4/3/17 | Cape Town City vs Chippa United | Premier League | 4:1 | Yes | Yes |
| 11/19/16 | Chippa United vs Cape Town City | Premier League | 1:2 | Yes | Yes |
| 1/30/16 | Cape Town City vs Chippa United | Premier League | 1:0 | No | No |
| 10/30/15 | Chippa United vs Cape Town City | Premier League | 2:1 | Yes | Yes |
| 5/6/15 | Cape Town City vs Chippa United | Premier League | 1:1 | No | Yes |
| 12/3/14 | Chippa United vs Cape Town City | Premier League | 2:2 | Yes | Yes |