| Date | Match | League | Result | OU 2.5 | Both to score |
|---|---|---|---|---|---|
| 9/26/26 | Chippa United U23 vs Stellenbosch U23 | 2. Snl | 0:0 | No | No |
| 3/22/26 | Stellenbosch U23 vs Chippa United U23 | 1st Division | 1:0 | No | No |
| 3/22/25 | Chippa United U23 vs Stellenbosch U23 | 2. Snl | 1:9 | Yes | Yes |
| 9/29/24 | Stellenbosch U23 vs Chippa United U23 | 1st Division | 4:1 | Yes | Yes |
| 2/3/24 | Chippa United U23 vs Stellenbosch U23 | Slovak Cup | 1:6 | Yes | Yes |
| 9/9/23 | Stellenbosch U23 vs Chippa United U23 | 2. Snl | 2:0 | No | No |
| 4/1/23 | Stellenbosch U23 vs Chippa United U23 | 1st Division | 2:1 | Yes | Yes |
| 10/1/22 | Chippa United U23 vs Stellenbosch U23 | 1st Division | 0:6 | Yes | No |
| 7/16/22 | Chippa United U23 vs Stellenbosch U23 | Multichoice Diski Shield - Play Offs | 0:1 | No | No |
| 3/26/22 | Stellenbosch U23 vs Chippa United U23 | 1st Division | 6:2 | Yes | Yes |
| 3/19/22 | Chippa United U23 vs Stellenbosch U23 | 1st Division | 3:3 | Yes | Yes |
| 5/15/21 | Stellenbosch U23 vs Chippa United U23 | 1st Division | 3:2 | Yes | Yes |