| 1 | Sat 3 Aug 2019 | 0-1 v Exeter CityExeter City 1-0 Macclesfield Town | Sky Bet League Two |
| 2 | Sat 10 Aug 2019 | 3-0 v Leyton OrientMacclesfield Town 3-0 Leyton Orient | Sky Bet League Two |
| 3 | Tue 13 Aug 2019 | 2-2 v BlackpoolBlackpool 2-2 Macclesfield Town | Carabao Cup First Round |
| 4 | Sat 17 Aug 2019 | 2-1 v Northampton TownNorthampton Town 1-2 Macclesfield Town | Sky Bet League Two |
| 5 | Tue 20 Aug 2019 | 0-1 v MorecambeMacclesfield Town 0-1 Morecambe | Sky Bet League Two |
| 6 | Sat 24 Aug 2019 | 1-0 v Scunthorpe UnitedMacclesfield Town 1-0 Scunthorpe United | Sky Bet League Two |
| 7 | Sat 31 Aug 2019 | 2-2 v StevenageStevenage 2-2 Macclesfield Town | Sky Bet League Two |
| 8 | Sat 7 Sep 2019 | 1-1 v Crawley TownMacclesfield Town 1-1 Crawley Town | Sky Bet League Two |
| 9 | Sat 14 Sep 2019 | 0-3 v Swindon TownSwindon Town 3-0 Macclesfield Town | Sky Bet League Two |
| 10 | Tue 17 Sep 2019 | 1-1 v Newport CountyMacclesfield Town 1-1 Newport County | Sky Bet League Two |
| 11 | Sat 21 Sep 2019 | 0-1 v Grimsby TownGrimsby Town 1-0 Macclesfield Town | Sky Bet League Two |
| 12 | Sat 28 Sep 2019 | 1-1 v Colchester UnitedMacclesfield Town 1-1 Colchester United | Sky Bet League Two |
| 13 | Sat 5 Oct 2019 | 2-2 v Cambridge UnitedCambridge United 2-2 Macclesfield Town | Sky Bet League Two |
| 14 | Sat 12 Oct 2019 | 2-1 v Port ValeMacclesfield Town 2-1 Port Vale | Sky Bet League Two |
| 15 | Sat 19 Oct 2019 | 1-0 v Oldham AthleticOldham Athletic 0-1 Macclesfield Town | Sky Bet League Two |
| 16 | Tue 22 Oct 2019 | 0-3 v Cheltenham TownCheltenham Town 3-0 Macclesfield Town | Sky Bet League Two |
| 17 | Sat 2 Nov 2019 | 1-2 v Carlisle UnitedCarlisle United 2-1 Macclesfield Town | Sky Bet League Two |
| 18 | Sat 16 Nov 2019 | 0-0 v Mansfield TownMacclesfield Town 0-0 Mansfield Town | Sky Bet League Two |
| 19 | Sat 23 Nov 2019 | 0-0 v Salford CitySalford City 0-0 Macclesfield Town | Sky Bet League Two |
| 20 | Sat 30 Nov 2019 | 1-1 v Bradford CityMacclesfield Town 1-1 Bradford City | Sky Bet League Two |
| 21 | Sat 14 Dec 2019 | 1-1 v WalsallWalsall 1-1 Macclesfield Town | Sky Bet League Two |
| 22 | Thu 26 Dec 2019 | 1-1 v Grimsby TownMacclesfield Town 1-1 Grimsby Town | Sky Bet League Two |
| 23 | Sun 29 Dec 2019 | 0-1 v Forest Green RoversForest Green Rovers 1-0 Macclesfield Town | Sky Bet League Two |
| 24 | Wed 1 Jan 2020 | 2-2 v Port ValePort Vale 2-2 Macclesfield Town | Sky Bet League Two |
| 25 | Sat 4 Jan 2020 | 1-0 v Cambridge UnitedMacclesfield Town 1-0 Cambridge United | Sky Bet League Two |
| 26 | Sat 18 Jan 2020 | 0-1 v Crewe AlexandraCrewe Alexandra 1-0 Cheltenham Town | Sky Bet League Two |
| 27 | Tue 28 Jan 2020 | 1-1 v Bradford CityBradford City 1-1 Cheltenham Town | Sky Bet League Two |
| 28 | Sat 1 Feb 2020 | 2-1 v MorecambeCheltenham Town 2-1 Morecambe | Sky Bet League Two |
| 29 | Sat 8 Feb 2020 | 0-1 v Scunthorpe UnitedScunthorpe United 1-0 Cheltenham Town | Sky Bet League Two |
| 30 | Tue 11 Feb 2020 | 1-0 v Carlisle UnitedCarlisle United 0-1 Cheltenham Town | Sky Bet League Two |
| 31 | Sat 15 Feb 2020 | 2-1 v Leyton OrientCheltenham Town 2-1 Leyton Orient | Sky Bet League Two |
| 32 | Sat 22 Feb 2020 | 1-0 v Mansfield TownCheltenham Town 1-0 Mansfield Town | Sky Bet League Two |
| 33 | Tue 25 Feb 2020 | 2-1 v Northampton TownCheltenham Town 2-1 Northampton Town | Sky Bet League Two |
| 34 | Sat 29 Feb 2020 | 2-0 v Colchester UnitedColchester United 0-2 Cheltenham Town | Sky Bet League Two |
| 35 | Sat 7 Mar 2020 | 0-0 v Port ValeCheltenham Town 0-0 Port Vale | Sky Bet League Two |
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