| Date | Competition | Home | | | | Away | Scored | MOTM | | | |
| 27/08/2023 | Premiership | Cleveland F.C |
6
|
V
|
2
| The Wynyard F.C | 0 |
|
|
|
|
| 10/09/2023 | Premiership | Cleveland F.C |
3
|
V
|
3
| Belle Vue Rovers F.C | 1 |
|
|
|
|
| 17/09/2023 | Premiership | Yarm Athletic F.C |
2
|
V
|
4
| Cleveland F.C | 0 |
|
|
|
|
| 24/09/2023 | Premiership | Cleveland F.C |
1
|
V
|
1
| Thornaby Nash F.C | 0 |
|
|
|
|
| 01/10/2023 | Premiership | Thornaby The Griffin FC |
4
|
V
|
1
| Cleveland F.C | 0 |
|
|
|
|
| 08/10/2023 | North Riding Sunday County Cup | Cleveland F.C |
1
|
V
|
3
| Grangetown Boys Club | 1 |
|
|
|
|
| 12/11/2023 | Premiership | Thornaby Nash F.C |
2
|
V
|
1
| Cleveland F.C | 0 |
|
|
|
|