| Sat 03/08/19 | Bootle v Hanley Town | 1-1 | | | | | |
| Tue 06/08/19 | Bootle v Skelmersdale United | 1-1 | | | | | |
| Sat 10/08/19 | Eccleshill United v Bootle | 2-1 | | | | | |
| Sat 17/08/19 | Runcorn Town v Bootle | 2-0 | | | | | |
| Tue 20/08/19 | Ashton Athletic v Bootle | 2-3 | | | | | |
| Mon 26/08/19 | Bootle v Burscough | 4-1 | | | | | |
| Sat 07/09/19 | Squires Gate v Bootle | 2-4 | | | | | |
| Sat 21/09/19 | Padiham v Bootle | 1-3 | | | | | |
| Sat 05/10/19 | Rylands v Bootle | 2-3 | | | | | |
| Tue 08/10/19 | Bootle v Whitchurch Alport | 1-0 | | | | | |
| Sat 12/10/19 | Rylands v Bootle | 3-0 | | | | | |
| Fri 18/10/19 | Bootle v Eccleshall | 3-2 | | | | | |
| Wed 06/11/19 | Bootle v Rylands | 3-1 | | | | | |
| Sat 09/11/19 | Litherland REMYCA v Bootle | 2-0 | | | | | |
| Sat 16/11/19 | Bootle v 1874 Northwich * | 1-4 | | | | | |
| Tue 26/11/19 | Bootle v Longridge Town | 3-2 | | | | | |
| Sat 30/11/19 | Bootle v Avro | 7-2 | | |  | | |
| Sat 14/12/19 | 1874 Northwich v Bootle | 2-0 | | | | | |
| Wed 18/12/19 | AFC Liverpool v Bootle | 1-4 | | | | | |
| Sat 21/12/19 | Burscough v Bootle | 0-5 | | | | | |
| Thu 26/12/19 | Bootle v Litherland REMYCA | 1-0 | | | | | |
| Sat 28/12/19 | Northwich Victoria v Bootle | 1-2 | | | | | |
| Fri 03/01/20 | Bootle v Squires Gate | 7-3 | | | | | |
| Tue 07/01/20 | Bootle v Runcorn Town | 4-0 | | | | | |
| Sat 11/01/20 | Congleton Town v Bootle | 0-3 | | | | | |
| Sat 25/01/20 | Whitchurch Alport v Bootle | 0-1 | | | | | |
| Sat 01/02/20 | Bootle v Ashton Athletic | 0-4 | | | | | |
| Tue 04/02/20 | Hanley Town v Bootle | 0-4 | | | | | |
| Sat 08/02/20 | Bootle v Rylands | 0-3 | | | | | |
| Sat 29/02/20 | Skelmersdale United v Bootle | 2-1 | | | | | |
| Tue 03/03/20 | Bootle v Skelmersdale United | 3-1 | | | | | |
| Sat 07/03/20 | Bootle v Irlam | 3-0 | | | | | |
