| 2023/03/07 | Boro Rangers |  | 1-2 |  | Scarborough Athletic | ||||
| 2023/03/08 | South Park Rangers |  | 2-1 |  | Guisborough Town |
| 2022/10/12 | Scarborough Athletic | | 4-1 |  | Middlesbrough S21 | ||||
| 2022/10/26 | Whitby Town |  | 2-0 |  | York City S21 | ||||
| 2022/11/15 | Redcar Town |  | 2-2 (4-3 pen.) |  | Redcar Athletic | ||||
| 2022/11/16 | Fishburn Park |  | 2-2 (3-4 pen.) | | Boro Rangers | ||||
| Northallerton Town |  | 2-0 |  | Pickering Town | |||||
| 2022/11/23 | Guisborough Town | | 5-1 |  | Richmond Town | ||||
| 2022/11/30 | Marske United |  | 2-2 (7-8 pen.) | | South Park Rangers | ||||
| 2022/12/21 | Thornaby |  | 4-1 |  | Redcar Newmarket |
