| Date | Match | League | Result | OU 2.5 | Both to score |
|---|---|---|---|---|---|
| 11/30/24 | Holywell vs Penrhyncoch | Division 1 | 2:1 | Yes | Yes |
| 9/14/24 | Penrhyncoch vs Holywell | Division 1 | 0:1 | No | No |
| 3/18/23 | Penrhyncoch vs Holywell | Division 1 | 0:5 | Yes | No |
| 10/1/22 | Holywell vs Penrhyncoch | Division 1 | 2:0 | No | No |
| 4/23/22 | Penrhyncoch vs Holywell | Division 1 | 1:3 | Yes | Yes |
| 11/20/21 | Holywell vs Penrhyncoch | Division 1 | 5:0 | Yes | No |
| 4/13/19 | Penrhyncoch vs Holywell | Division 1 | 3:3 | Yes | Yes |
| 8/18/18 | Holywell vs Penrhyncoch | Division 1 | 2:3 | Yes | Yes |
| 8/11/18 | Holywell vs Penrhyncoch | Club Friendly | 1:0 | No | No |
| 5/5/18 | Penrhyncoch vs Holywell | Division 1 | 1:0 | No | No |
| 4/14/18 | Holywell vs Penrhyncoch | Division 1 | 1:1 | No | Yes |
| 1/18/18 | Penrhyncoch vs Holywell | Club Friendly | 3:1 | Yes | Yes |
| 12/17/16 | Penrhyncoch vs Holywell | Division 1 | 1:1 | No | Yes |
| 8/27/16 | Holywell vs Penrhyncoch | Division 1 | 1:1 | No | Yes |
| 4/1/06 | Penrhyncoch vs Holywell | Division 1 | 0:2 | No | No |
| 11/12/05 | Holywell vs Penrhyncoch | Division 1 | 3:0 | Yes | No |