| Sat 03/08/19 | Rylands v Charnock Richard | 3-2 | | | | | |
| Wed 07/08/19 | Litherland REMYCA v Rylands | 0-3 |  | | | | |
| Sat 10/08/19 | Runcorn Town v Rylands | 2-0 | | | | | |
| Sat 17/08/19 | Rylands v Avro | 5-0 | | | | | |
| Tue 20/08/19 | Burscough v Rylands | 0-0 | | | | | |
| Mon 26/08/19 | Rylands v Ashton Athletic | 2-1 | | | | | |
| Sat 31/08/19 | Rylands v Athersley Recreation * | 6-0 | | | | | |
| Sat 07/09/19 | Winsford United v Rylands | 0-2 | | | | | |
| Sat 14/09/19 | Rylands v Rossington Main | 4-2 | | | | | |
| Sat 21/09/19 | Rylands v Congleton Town | 4-2 | | | | | |
| Sat 28/09/19 | Hanley Town v Rylands | 2-1 | | | | | |
| Wed 02/10/19 | Longridge Town v Rylands | 4-1 | | | | | |
| Sat 05/10/19 | Rylands v Bootle | 2-3 | | | | |  |
| Tue 08/10/19 | Rylands v Northwich Victoria | 1-2 | | | | | |
| Sat 12/10/19 | Rylands v Bootle | 3-0 | | | | | |
| Fri 18/10/19 | Rylands v Barnton | 5-0 | | | | | |
| Sat 02/11/19 | Rylands v Grimsby Borough | 0-1 | | | | | |
| Wed 06/11/19 | Bootle v Rylands | 3-1 | | | | | |
| Sat 09/11/19 | Rylands v Padiham | 4-3 | | | | | |
| Sat 16/11/19 | Ashton Athletic v Rylands | 1-3 | | | | | |
| Sat 23/11/19 | Squires Gate v Rylands | 0-3 | | | | | |
| Tue 26/11/19 | Rylands v Whitchurch Alport | 2-1 | | | | | |
| Sat 07/12/19 | Rylands v 1874 Northwich | 1-1 | | | | | |
| Tue 17/12/19 | Padiham v Rylands | 1-3 | | | | | |
| Sat 21/12/19 | Avro v Rylands | 0-1 | | | | | |
| Thu 26/12/19 | Rylands v Runcorn Town | 1-1 | | | | | |
| Sat 28/12/19 | 1874 Northwich v Rylands | 2-1 | | | | | |
| Sat 04/01/20 | Rylands v Barnoldswick Town | 0-1 | | | | | |
| Tue 07/01/20 | Irlam v Rylands | 1-2 | | | | | |
| Sat 11/01/20 | Charnock Richard v Rylands | 3-1 | | | | | |
| Sat 18/01/20 | Rylands v Padiham | 5-1 | | | | | |
| Sat 25/01/20 | Northwich Victoria v Rylands | 0-2 | | | | | |
| Tue 28/01/20 | Rylands v Irlam | 1-0 | | | | | |
| Sat 01/02/20 | Rylands v Squires Gate | 2-1 | | | | | |
| Tue 04/02/20 | Skelmersdale United v Rylands | 2-3 | | | | | |
| Sat 08/02/20 | Bootle v Rylands | 0-3 | | | | | |
| Sat 15/02/20 | Rylands v Skelmersdale United | 2-0 | | | | | |
| Sat 22/02/20 | Rylands v Litherland REMYCA | 1-1 | | | | | |
| Sat 07/03/20 | Whitchurch Alport v Rylands | 0-2 | | | | | |
