| Date | Competition | Home | | | | Away | Scored | MOTM | | | |
| 22/10/2023 | Ian Gorman Memorial Trophy Second Round | The Wynyard F.C |
7
|
V
|
3
| Yarm Albion F.C | 0 |
|
|
|
|
| 14/01/2024 | Premiership | The Wynyard F.C |
4
|
V
|
5
| Thornaby Nash F.C | 0 |
|
|
|
|
| 21/01/2024 | Premiership | The Wynyard F.C |
1
|
V
|
3
| Yarm Athletic F.C | 0 |
MOTM
|
|
|
|
| 30/04/2024 | Premiership | Norton George And Dragon |
9
|
V
|
2
| The Wynyard F.C | 0 |
|
|
|
|
| 07/05/2024 | Premiership | Coulby Newham F.C |
0
|
V
|
4
| The Wynyard F.C | 0 |
|
|
|
|
| 10/05/2024 | John Jackson Memorial Trophy Final | Norton George And Dragon |
3
|
V
|
0
| The Wynyard F.C | 0 |
|
|
|
|