| Date | Competition | Home | | | | Away | Scored | MOTM | | | |
| 20/08/2023 | Division One | Beckfields F.C |
4
|
V
|
1
| Penny Black F.C | 0 |
|
|
|
|
| 27/08/2023 | Division One | Penny Black F.C |
3
|
V
|
4
| Rimswell F.C | 0 |
|
|
-
|
|
| 03/09/2023 | Durham Sunday Cup | Penny Black F.C |
3
|
V
|
4
| HARTLEPOOL ESKIMO JOE'S | 0 |
|
|
|
|
| 10/09/2023 | Alan Close Round One | Darlington Young Bulls F.C |
2
|
V
|
4
| Penny Black F.C | 0 |
|
|
|
|
| 24/09/2023 | Heart Foundation Cup | Penny Black F.C |
2
|
V
|
2
| North Bitchburn Red Lion F.C | 0 |
|
|
|
|
| 01/10/2023 | Division One | Penny Black F.C |
1
|
V
|
2
| Beckfields F.C | 0 |
|
|
|
|
| 15/10/2023 | Heart Foundation Cup | Penny Black F.C |
0
|
V
|
8
| Brandon Sports Club | 0 |
|
|
|
|
| 22/10/2023 | Ian Gorman Memorial Trophy Second Round | Penny Black F.C |
3
|
V
|
3
| Norton George And Dragon | 0 |
|
|
|
|
| 19/11/2023 | Division One | Penny Black F.C |
10
|
V
|
3
| Billingham Salutation F.C | 1 |
|
|
|
|
| 17/12/2023 | Division One | Billingham Town U23's |
3
|
V
|
4
| Penny Black F.C | 0 |
|
|
|
|
| 21/01/2024 | Division One | Darlington Young Bulls F.C |
3
|
V
|
2
| Penny Black F.C | 0 |
|
|
|
|
| 28/01/2024 | Division One | Billingham Salutation F.C |
3
|
V
|
6
| Penny Black F.C | 0 |
|
|
|
|
| 25/02/2024 | Alan Close Round Two | Fox Covert F.C |
6
|
V
|
3
| Penny Black F.C | 0 |
MOTM
|
|
|
|
| 03/03/2024 | Division One | Penny Black F.C |
7
|
V
|
1
| Middleton Rangers F.C | 0 |
MOTM
|
|
|
|
| 17/03/2024 | Division One | Penny Black F.C |
5
|
V
|
0
| Darlington Young Bulls F.C | 0 |
|
|
|
|
| 24/03/2024 | Ian Gorman Memorial Trophy Third Round | Penny Black F.C |
2
|
V
|
3
| Fox Covert F.C | 0 |
|
|
|
|
| 07/04/2024 | Division One | St Marys 1947 Sunday F.C |
1
|
V
|
3
| Penny Black F.C | 0 |
MOTM
|
|
|
|
| 11/04/2024 | Division One | Rimswell F.C |
5
|
V
|
2
| Penny Black F.C | 0 |
|
|
|
|
| 14/04/2024 | Division One | Penny Black F.C |
2
|
V
|
2
| St Marys 1947 Sunday F.C | 0 |
|
|
|
|
| 18/04/2024 | Division One | Penny Black F.C |
3
|
V
|
4
| Billingham Town U23's | 0 |
|
|
|
|
| 23/04/2024 | Division One | Fox Covert F.C |
6
|
V
|
0
| Penny Black F.C | 0 |
|
|
|
|
| 25/04/2024 | Division One | Penny Black F.C |
1
|
V
|
4
| Fox Covert F.C | 0 |
|
|
|
|
| 28/04/2024 | Division One | Middleton Rangers F.C |
3
|
V
|
6
| Penny Black F.C | 0 |
|
|
|
|