| Pre | | Cleethorpes Town | Sat 06/07/2019 | 15:00 | The Linden Homes Club | 8‑0 | 2,034 | | |
| Pre | | Grantham Town | Tue 09/07/2019 | 19:30 | South Kesteven Sports Stadium | 3‑1 | | | |
| Pre | | Boston United | Thu 11/07/2019 | 19:30 | York Street | 1‑2 | 682 | | |
| Pre | | Gainsborough Trinity | Thu 18/07/2019 | 19:30 | The Gainsborough Martin & Co. Arena | 0‑2 | 439 | | |
| Pre | | Doncaster Rovers | Sat 20/07/2019 | 12:00 | Blundell Park | 1‑0 | 1,331 | | |
| Pre | | Scarborough Athletic | Tue 23/07/2019 | 19:30 | Flamingo Land Stadium | 2‑1 | 705 | | |
| Pre | | Peterborough United | Sat 27/07/2019 | 15:00 | Blundell Park | 0‑2 | 1,573 | | |
| League | | Morecambe | Sat 03/08/2019 | 15:00 | Globe Arena | 2‑0 | 2,872 | Report | Thread |
| League | | Bradford | Sat 10/08/2019 | 13:00 | Blundell Park | 1‑1 | 6,882 | Report | Thread |
| EFLC | R1 | Doncaster | Tue 13/08/2019 | 19:45 | Blundell Park | 1‑0 | 2,470 | Report | Thread |
| League | | Forest Green | Sat 17/08/2019 | 15:00 | The Lawn | 0‑1 | 2,152 | Report | Thread |
| League | | Colchester | Tue 20/08/2019 | 19:45 | Blundell Park | 2‑2 | 4,103 | Report | Thread |
| League | | Port Vale | Sat 24/08/2019 | 15:00 | Blundell Park | 5‑2 | 4,290 | Report | Thread |
| League | | Walsall | Sat 31/08/2019 | 15:00 | Bescot Stadium | 3‑1 | 4,812 | Report | Thread |
| EFLT | 1A | Scunthorpe | Tue 03/09/2019 | 19:45 | Blundell Park | 1‑2 | 1,302 | | Thread |
| League | | Crewe | Sat 07/09/2019 | 15:00 | Blundell Park | 0‑2 | 4,679 | Report | Thread |
| EFLC | R2 | Macclesfield | Tue 10/09/2019 | 19:45 | Blundell Park | 0‑0 | 3,011 | Report | Thread |
| League | | Oldham | Sat 14/09/2019 | 15:00 | Boundary Park | 2‑2 | 3,789 | Report | Thread |
| League | | Salford | Tue 17/09/2019 | 19:45 | Moor Lane | 0‑1 | 2,782 | Report | Thread |
| League | | Macclesfield | Sat 21/09/2019 | 15:00 | Blundell Park | 1‑0 | 3,794 | Report | Thread |
| EFLC | R3 | Chelsea | Wed 25/09/2019 | 19:45 | Stamford Bridge | 1‑7 | 39,674 | Report | Thread |
| League | | Exeter | Sat 28/09/2019 | 15:00 | St James Park | 3‑1 | 4,973 | Report | Thread |
| League | | Mansfield | Sat 05/10/2019 | 15:00 | Blundell Park | 0‑1 | 5,087 | Report | Thread |
| EFLT | 1B | Sunderland | Tue 08/10/2019 | 19:45 | Stadium of Light | 2‑3 | 6,952 | | Thread |
| League | | Stevenage | Sat 12/10/2019 | 15:00 | Broadhall Way | 1‑2 | 3,220 | Report | Thread |
| League | | Leyton Orient | Sat 19/10/2019 | 15:00 | Blundell Park | 0‑4 | 4,132 | Report | Thread |
| League | | Cambridge Utd | Tue 22/10/2019 | 19:45 | Abbey Stadium | 0‑0 | 4,898 | Report | Thread |
| EFLT | 1C | Leicester U21 | Tue 29/10/2019 | 19:45 | Blundell Park | 1‑2 | 341 | | Thread |
| League | | Plymouth | Sat 02/11/2019 | 15:00 | Home Park | P‑P | | | |
| FAC | R1 | Newport County | Sat 09/11/2019 | 15:00 | Blundell Park | 1‑1 | 2,086 | Report | Thread |
| League | | Newport County | Sat 16/11/2019 | 15:00 | Blundell Park | P‑P | | | |
| FAC | R1R | Newport County | Wed 20/11/2019 | 19:45 | | 0‑2 | 2,053 | Report | |
| League | | Northampton | Sat 23/11/2019 | 15:00 | Sixfields | 0‑2 | 5,211 | Report | |
| League | | Cheltenham | Tue 26/11/2019 | 19:45 | Blundell Park | 0‑0 | 2,508 | | Thread |
| League | | Swindon | Sat 07/12/2019 | 15:00 | Blundell Park | – | | | |
| League | | Carlisle | Sat 14/12/2019 | 15:00 | Brunton Park | – | | | |
| League | | Scunthorpe | Sat 21/12/2019 | 13:00 | Blundell Park | – | | | |
| League | | Macclesfield | Thu 26/12/2019 | 15:00 | Moss Rose | – | | | |
| League | | Crawley Town | Sun 29/12/2019 | 15:00 | Blundell Park | – | | | |
| League | | Salford | Wed 01/01/2020 | 15:00 | Blundell Park | – | | | |
| League | | Mansfield | Sat 04/01/2020 | 15:00 | Field Mill | – | | | |
| League | | Leyton Orient | Sat 11/01/2020 | 15:00 | Brisbane Road | – | | | |
| League | | Exeter | Sat 18/01/2020 | 15:00 | Blundell Park | – | | | |
| League | | Crawley Town | Sat 25/01/2020 | 15:00 | Broadfield Stadium | – | | | |
| League | | Stevenage | Tue 28/01/2020 | 19:45 | Blundell Park | – | | | |
| League | | Forest Green | Sat 01/02/2020 | 15:00 | Blundell Park | – | | | |
| League | | Bradford | Sat 08/02/2020 | 15:00 | Valley Parade | – | | | |
| League | | Colchester | Tue 11/02/2020 | 19:45 | Weston Homes | – | | | |
| League | | Morecambe | Sat 15/02/2020 | 15:00 | Blundell Park | – | | | |
| League | | Swindon | Sat 22/02/2020 | 15:00 | County Ground | – | | | |
| League | | Northampton | Sat 29/02/2020 | 15:00 | Blundell Park | – | | | |
| League | | Scunthorpe | Sat 07/03/2020 | 13:00 | Glanford Park | – | | | |
| League | | Carlisle | Sat 14/03/2020 | 15:00 | Blundell Park | – | | | |
| League | | Cambridge Utd | Tue 17/03/2020 | 19:45 | Blundell Park | – | | | |
| League | | Cheltenham | Sat 21/03/2020 | 15:00 | Whaddon Road | – | | | |
| League | | Plymouth | Sat 28/03/2020 | 15:00 | Blundell Park | – | | | |
| League | | Newport County | Sat 04/04/2020 | 15:00 | Newport Stadium | – | | | |
| League | | Port Vale | Fri 10/04/2020 | 15:00 | Vale Park | – | | | |
| League | | Walsall | Mon 13/04/2020 | 15:00 | Blundell Park | – | | | |
| League | | Crewe | Sat 18/04/2020 | 15:00 | Gresty Road | – | | | |
| League | | Oldham | Sat 25/04/2020 | 15:00 | Blundell Park | – | | | |
Last Year's Results |
All League Two Fixtures
