| 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 | 0 |
|
|
|
|
| 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 | 0 |
|
|
|
|
| 15/10/2023 | Premiership | Cleveland F.C |
3
|
V
|
3
| Yarm Albion F.C | 0 |
|
|
|
|
| 12/11/2023 | Premiership | Thornaby Nash F.C |
2
|
V
|
1
| Cleveland F.C | 0 |
|
|
|
|
| 26/11/2023 | Ian Gorman Memorial Trophy Second Round | Cleveland F.C |
4
|
V
|
1
| Darlington Young Bulls F.C | 0 |
|
|
|
|
| 07/01/2024 | Premiership | Cleveland F.C |
0
|
V
|
3
| Thornaby The Griffin FC | 0 |
|
|
|
|
| 14/01/2024 | Premiership | Cleveland F.C |
2
|
V
|
0
| Yarm Athletic F.C | 0 |
MOTM
|
|
-
|
|
| 21/01/2024 | John Jackson Memorial Trophy Round Two | Cleveland F.C |
2
|
V
|
1
| Thornaby The Griffin FC | 0 |
|
|
|
|
| 25/02/2024 | Premiership | Cleveland F.C |
5
|
V
|
5
| Village Park Rangers F.C | 0 |
|
|
|
|
| 10/03/2024 | Premiership | Yarm Albion F.C |
0
|
V
|
4
| Cleveland F.C | 0 |
|
|
|
|
| 17/03/2024 | Premiership | Village Park Rangers F.C |
5
|
V
|
2
| Cleveland F.C | 0 |
|
|
|
|
| 07/04/2024 | John Jackson Memorial Trophy Semi Final | Cleveland F.C |
1
|
V
|
2
| The Wynyard F.C | 0 |
|
|
|
|
| 14/04/2024 | Premiership | Coulby Newham F.C |
2
|
V
|
4
| Cleveland F.C | 0 |
|
|
|
|
| 28/04/2024 | Premiership | The Wynyard F.C |
2
|
V
|
5
| Cleveland F.C | 0 |
|
|
|
|