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| Date | Match | Score |
|---|---|---|
| 01.02.2026 | Chippa United U23 - Maritzburg United U23 | 0 : 2 |
| 15.11.2025 | Maritzburg United U23 - Chippa United U23 | 1 : 1 |
| 25.03.2023 | Chippa United U23 - Maritzburg United U23 | 1 : 2 |
| 29.01.2023 | Maritzburg United U23 - Chippa United U23 | 1 : 0 |
| 16.04.2022 | Maritzburg United U23 - Chippa United U23 | 3 : 6 |
| 12.02.2022 | Chippa United U23 - Maritzburg United U23 | 0 : 0 |
| 10.04.2021 | Maritzburg United U23 - Chippa United U23 | 4 : 2 |
| Date | Match | Score | Res |
|---|---|---|---|
| 09.05.2026 | Magesi U23 - Maritzburg United U23 | 2 - 2 | D |
| 02.05.2026 | Maritzburg United U23 - AmaZulu U23 | 1 - 3 | L |
| 25.04.2026 | Maritzburg United U23 - Orbit College U23 | 0 - 0 | D |
| 18.04.2026 | TS Galaxy U23 - Maritzburg United U23 | 0 - 3 | W |
| 11.04.2026 | Golden Arrows U23 - Maritzburg United U23 | 1 - 4 | W |
| Date | Match | Score | Res |
|---|---|---|---|
| 09.05.2026 | Kaizer Chiefs U23 - Chippa United U23 | 11 - 0 | L |
| 02.05.2026 | Chippa United U23 - Orlando Pirates U23 | 0 - 2 | L |
| 26.04.2026 | AmaZulu U23 - Chippa United U23 | 2 - 1 | L |
| 18.04.2026 | Mamelodi Sundowns U23 - Chippa United U23 | 3 - 2 | L |
| 12.04.2026 | Chippa United U23 - Polokwane City U23 | 0 - 0 | D |