| Tuesday, 12 September 2023 03:30
|
| DaCosta Cup | DeCarteret College | 3 | - | 0 | Mt. St. Joseph Catholic | |
| Friday, 15 September 2023 03:30
|
| DaCosta Cup | Manchester | 5 | - | 0 | DeCarteret College | |
| Wednesday, 20 September 2023 03:30
|
| DaCosta Cup | Belair | 1 | - | 0 | DeCarteret College | |
| Saturday, 23 September 2023 03:30
|
| DaCosta Cup | DeCarteret College | 8 | - | 0 | Cross Keys | |
| Tuesday, 26 September 2023 03:30
|
| DaCosta Cup | May Day | | - | | DeCarteret College | |
| Wednesday, 27 September 2023 03:30
|
| DaCosta Cup | May Day | 0 | - | 3 | DeCarteret College | |
| Thursday, 28 September 2023 03:30
|
| DaCosta Cup | May Day | | - | | DeCarteret College | |
| Friday, 29 September 2023 03:30
|
| DaCosta Cup | Mt. St Joseph | 0 | - | 6 | DeCarteret College | |
| Saturday, 30 September 2023 03:30
|
| DaCosta Cup | DeCarteret College | 6 | - | 0 | Mt. St Joseph | |
| Monday, 02 October 2023 03:30
|
| DaCosta Cup | DeCarteret College | | - | | Manchester | |
| Thursday, 05 October 2023 03:30
|
| DaCosta Cup | DeCarteret College | 0 | - | 2 | Belair | |
| Saturday, 07 October 2023 03:30
|
| DaCosta Cup | May Day | 0 | - | 4 | DeCarteret College | |
| Thursday, 12 October 2023 03:00
|
| DaCosta Cup | DeCarteret College | 0 | - | 1 | Manchester | |
| Saturday, 14 October 2023 01:30
|
| DaCosta Cup | DeCarteret College | 1 | - | 2 | May Day | |
| Saturday, 21 October 2023 01:30
|
| DaCosta Cup | DeCarteret College | 0 | - | 8 | Clarendon College | |
| Wednesday, 25 October 2023 03:30
|
| DaCosta Cup | Clarendon College | 4 | - | 1 | DeCarteret College | |
| Wednesday, 01 November 2023 03:00
|
| DaCosta Cup | Christiana | 0 | - | 1 | DeCarteret College | |
SB Football 
