| 2024/05/13 | Boro Rangers |  | 1-5 |  | Whitby Town |
| 2024/03/12 | Guisborough Town |  | 1-1 (2-4 pens) | | Whitby Town | ||||
| 2024/03/26 | Redcar Athletic |  | 0-5 | | Boro Rangers |
| 2024/01/30 | Boro Rangers | | 1-0 |  | Pickering Town | ||||
| 2024/02/07 | Marske United |  | WO | | Whitby Town | ||||
| 2024/02/13 | Guisborough Town | | 1-1 (3-2 pens) |  | Scarborough Athletic | ||||
| 2024/02/20 | Redcar Athletic | | 1-0 |  | Richmond Town |
| 2023/10/10 | Middlesbrough U21 |  | 1-1 (7-8 pens) | | Scarborough Athletic | ||||
| 2023/10/17 | Redcar Athletic | | 4-0 |  | Thornaby | ||||
| 2023/11/01 | Guisborough Town | | 3-2 |  | York City U21 | ||||
| 2023/11/21 | Yarm & Eaglescliffe FC |  | 4-5 | | Marske United | ||||
| Pickering Town | | 5-2 |  | Fishburn Park | |||||
| 2023/11/22 | Cleveland FC |  | 1-2 | | Richmond Town | ||||
| 2023/12/06 | Redcar Town |  | 2-3 | | Boro Rangers | ||||
| 2024/02/06 | Northallerton Town |  | 1-3 | | Whitby Town |
| 2023/10/03 | Fishburn Park | | 5-1 |  | Kader FC | ||||
| 2023/10/07 | Richmond Town | | 3-2 |  | Grangetown Boys | ||||
| 2023/10/18 | St Mary´s 1947 |  | 2-3 | | Cleveland FC |
