| 1 | Sat 3 Aug 2019 | 30-1 v Exeter CityExeter City 1-0 Macclesfield Town | Sky Bet League Two |
| 2 | Tue 24 Sep 2019 | 32-3 v Port ValeMacclesfield Town 2-3 Port Vale | Leasing.com Trophy Northern Group D |
| 3 | Sat 5 Oct 2019 | 32-2 v Cambridge UnitedCambridge United 2-2 Macclesfield Town | Sky Bet League Two |
| 4 | Sat 16 Nov 2019 | 3 0-0 v Mansfield TownMacclesfield Town 0-0 Mansfield Town | Sky Bet League Two |
| 5 | Sat 23 Nov 2019 | 30-0 v Salford CitySalford City 0-0 Macclesfield Town | Sky Bet League Two |
| 6 | Sat 30 Nov 2019 | 3 1-1 v Bradford CityMacclesfield Town 1-1 Bradford City | Sky Bet League Two |
| 7 | Sat 14 Dec 2019 | 31-1 v WalsallWalsall 1-1 Macclesfield Town | Sky Bet League Two |
| 8 | Thu 26 Dec 2019 | 3 1-1 v Grimsby TownMacclesfield Town 1-1 Grimsby Town | Sky Bet League Two |
| 9 | Sun 29 Dec 2019 | 30-1 v Forest Green RoversForest Green Rovers 1-0 Macclesfield Town | Sky Bet League Two |
| 10 | Wed 1 Jan 2020 | 32-2 v Port ValePort Vale 2-2 Macclesfield Town | Sky Bet League Two |
| 11 | Sat 4 Jan 2020 | 31-0 v Cambridge UnitedMacclesfield Town 1-0 Cambridge United | Sky Bet League Two |
| 12 | Sat 11 Jan 2020 | 31-1 v Oldham AthleticMacclesfield Town 1-1 Oldham Athletic | Sky Bet League Two |
| 13 | Sat 18 Jan 2020 | 3 1-2 v Colchester UnitedColchester United 2-1 Macclesfield Town | Sky Bet League Two |
| 14 | Sat 1 Feb 2020 | 30-1 v Northampton TownMacclesfield Town 0-1 Northampton Town | Sky Bet League Two |
| 15 | Sat 8 Feb 2020 | 31-1 v Leyton OrientLeyton Orient 1-1 Macclesfield Town | Sky Bet League Two |
| 16 | Tue 11 Feb 2020 | 30-2 v MorecambeMorecambe 2-0 Macclesfield Town | Sky Bet League Two |
| 17 | Sat 15 Feb 2020 | 32-3 v Exeter CityMacclesfield Town 2-3 Exeter City | Sky Bet League Two |
| 18 | Tue 18 Feb 2020 | 31-1 v Plymouth ArgyleMacclesfield Town 1-1 Plymouth Argyle | Sky Bet League Two |
| 19 | Sat 7 Mar 2020 | 30-3 v Plymouth ArgylePlymouth Argyle 3-0 Macclesfield Town | Sky Bet League Two |
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