| 1 | Sat 3 Aug 2019 | 12 0-3 v Plymouth ArgyleCrewe Alexandra 0-3 Plymouth Argyle | Sky Bet League Two |
| 2 | Sat 10 Aug 2019 | 122-1 v Oldham AthleticOldham Athletic 1-2 Crewe Alexandra | Sky Bet League Two |
| 3 | Tue 13 Aug 2019 | 122-2 v MiddlesbroughMiddlesbrough 2-2 Crewe Alexandra | Carabao Cup First Round |
| 4 | Sat 17 Aug 2019 | 121-0 v WalsallCrewe Alexandra 1-0 Walsall | Sky Bet League Two |
| 5 | Tue 20 Aug 2019 | 122-1 v Crawley TownCrawley Town 1-2 Crewe Alexandra | Sky Bet League Two |
| 6 | Sat 24 Aug 2019 | 120-1 v Newport CountyNewport County 1-0 Crewe Alexandra | Sky Bet League Two |
| 7 | Tue 27 Aug 2019 | 121-6 v Aston VillaCrewe Alexandra 1-6 Aston Villa | Carabao Cup Second Round |
| 8 | Sat 31 Aug 2019 | 122-1 v Bradford CityCrewe Alexandra 2-1 Bradford City | Sky Bet League Two |
| 9 | Sat 7 Sep 2019 | 122-0 v Grimsby TownGrimsby Town 0-2 Crewe Alexandra | Sky Bet League Two |
| 10 | Sat 14 Sep 2019 | 122-3 v Cambridge UnitedCrewe Alexandra 2-3 Cambridge United | Sky Bet League Two |
| 11 | Tue 17 Sep 2019 | 122-1 v Leyton OrientLeyton Orient 1-2 Crewe Alexandra | Sky Bet League Two |
| 12 | Sat 21 Sep 2019 | 124-1 v Salford CityCrewe Alexandra 4-1 Salford City | Sky Bet League Two |
| 13 | Sat 28 Sep 2019 | 121-1 v Cheltenham TownCheltenham Town 1-1 Crewe Alexandra | Sky Bet League Two |
| 14 | Sat 5 Oct 2019 | 121-1 v Exeter CityCrewe Alexandra 1-1 Exeter City | Sky Bet League Two |
| 15 | Sat 12 Oct 2019 | 12 4-2 v Carlisle UnitedCarlisle United 2-4 Crewe Alexandra | Sky Bet League Two |
| 16 | Sat 19 Oct 2019 | 123-1 v Swindon TownCrewe Alexandra 3-1 Swindon Town | Sky Bet League Two |
| 17 | Tue 22 Oct 2019 | 120-0 v Colchester UnitedCrewe Alexandra 0-0 Colchester United | Sky Bet League Two |
| 18 | Sat 2 Nov 2019 | 120-1 v Port ValeCrewe Alexandra 0-1 Port Vale | Sky Bet League Two |
| 19 | Tue 26 Nov 2019 | 120-0 v Forest Green RoversForest Green Rovers 0-0 Crewe Alexandra | Sky Bet League Two |
| 20 | Sat 30 Nov 2019 | 121-1 v EastleighEastleigh 1-1 Crewe Alexandra | Emirates FA Cup Second Round |
| 21 | Tue 10 Dec 2019 | 123-1 v EastleighCrewe Alexandra 3-1 Eastleigh | Emirates FA Cup Second Round |
| 22 | Sat 14 Dec 2019 | 121-1 v Mansfield TownCrewe Alexandra 1-1 Mansfield Town | Sky Bet League Two |
| 23 | Sat 21 Dec 2019 | 125-1 v StevenageStevenage 1-5 Crewe Alexandra | Sky Bet League Two |
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