| 1 | Sat 3 Aug 2019 | 0-3 v Plymouth ArgyleCrewe Alexandra 0-3 Plymouth Argyle | Sky Bet League Two |
| 2 | Sat 10 Aug 2019 | 2-1 v Oldham AthleticOldham Athletic 1-2 Crewe Alexandra | Sky Bet League Two |
| 3 | Sat 17 Aug 2019 | 1-0 v WalsallCrewe Alexandra 1-0 Walsall | Sky Bet League Two |
| 4 | Tue 20 Aug 2019 | 2-1 v Crawley TownCrawley Town 1-2 Crewe Alexandra | Sky Bet League Two |
| 5 | Sat 24 Aug 2019 | 0-1 v Newport CountyNewport County 1-0 Crewe Alexandra | Sky Bet League Two |
| 6 | Sat 31 Aug 2019 | 2-1 v Bradford CityCrewe Alexandra 2-1 Bradford City | Sky Bet League Two |
| 7 | Sat 7 Sep 2019 | 2-0 v Grimsby TownGrimsby Town 0-2 Crewe Alexandra | Sky Bet League Two |
| 8 | Sat 14 Sep 2019 | 2-3 v Cambridge UnitedCrewe Alexandra 2-3 Cambridge United | Sky Bet League Two |
| 9 | Tue 17 Sep 2019 | 2-1 v Leyton OrientLeyton Orient 1-2 Crewe Alexandra | Sky Bet League Two |
| 10 | Sat 21 Sep 2019 | 4-1 v Salford CityCrewe Alexandra 4-1 Salford City | Sky Bet League Two |
| 11 | Sat 28 Sep 2019 | 1-1 v Cheltenham TownCheltenham Town 1-1 Crewe Alexandra | Sky Bet League Two |
| 12 | Sat 5 Oct 2019 | 1-1 v Exeter CityCrewe Alexandra 1-1 Exeter City | Sky Bet League Two |
| 13 | Sat 12 Oct 2019 | 4-2 v Carlisle UnitedCarlisle United 2-4 Crewe Alexandra | Sky Bet League Two |
| 14 | Sat 16 Nov 2019 | 1-4 v Northampton TownNorthampton Town 4-1 Crewe Alexandra | Sky Bet League Two |
| 15 | Tue 26 Nov 2019 | 0-0 v Forest Green RoversForest Green Rovers 0-0 Crewe Alexandra | Sky Bet League Two |
| 16 | Sat 30 Nov 2019 | 1-1 v EastleighEastleigh 1-1 Crewe Alexandra | Emirates FA Cup Second Round |
| 17 | Tue 10 Dec 2019 | 3-1 v EastleighCrewe Alexandra 3-1 Eastleigh | Emirates FA Cup Second Round |
| 18 | Sat 14 Dec 2019 | 1-1 v Mansfield TownCrewe Alexandra 1-1 Mansfield Town | Sky Bet League Two |
| 19 | Sat 21 Dec 2019 | 5-1 v StevenageStevenage 1-5 Crewe Alexandra | Sky Bet League Two |
| 20 | Thu 26 Dec 2019 | 1-3 v Salford CitySalford City 3-1 Crewe Alexandra | Sky Bet League Two |
| 21 | Sun 29 Dec 2019 | 3-1 v Scunthorpe UnitedCrewe Alexandra 3-1 Scunthorpe United | Sky Bet League Two |
| 22 | Wed 1 Jan 2020 | 4-1 v Carlisle UnitedCrewe Alexandra 4-1 Carlisle United | Sky Bet League Two |
| 23 | Sun 5 Jan 2020 | 1-3 v BarnsleyCrewe Alexandra 1-3 Barnsley | Emirates FA Cup Third Round |
| 24 | Sat 11 Jan 2020 | 1-3 v Swindon TownSwindon Town 3-1 Crewe Alexandra | Sky Bet League Two |
| 25 | Sat 1 Feb 2020 | 2-1 v WalsallWalsall 1-2 Crewe Alexandra | Sky Bet League Two |
| 26 | Sat 8 Feb 2020 | 2-1 v Oldham AthleticCrewe Alexandra 2-1 Oldham Athletic | Sky Bet League Two |
| 27 | Sat 22 Feb 2020 | 2-0 v Macclesfield TownCrewe Alexandra 2-0 Macclesfield Town | Sky Bet League Two |
| 28 | Sat 29 Feb 2020 | 1-1 v MorecambeMorecambe 1-1 Crewe Alexandra | Sky Bet League Two |
| 29 | Tue 3 Mar 2020 | 1-1 v Exeter CityExeter City 1-1 Crewe Alexandra | Sky Bet League Two |
| 30 | Sat 7 Mar 2020 | 3-1 v StevenageCrewe Alexandra 3-1 Stevenage | Sky Bet League Two |
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