| 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 |
|
|
|
|
| 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 |
|
|
-
|
|
| 28/01/2024 | Premiership | Norton George And Dragon |
6
|
V
|
1
| Cleveland F.C | 0 |
|
|
|
|
| 17/03/2024 | Premiership | Village Park Rangers F.C |
5
|
V
|
2
| Cleveland F.C | 0 |
|
|
-
|
|
| 24/03/2024 | Premiership | Cleveland F.C |
5
|
V
|
0
| Coulby Newham F.C | 0 |
|
|
|
|