Weather: Rainy Stadium: Jonny-Rocks Stadium Pitch: Good Round: 30
Referee: Anthony Backhouse Home Manager: Michael James Duff Away Manager: Sol Campbell
| England League 2 | 2018/08/21 18:45 | Macclesfield v Cheltenham | D | 1-1 |
| England National League | 2016/04/23 14:00 | Macclesfield v Cheltenham | W | 0-1 |
| England National League | 2015/09/15 18:45 | Cheltenham v Macclesfield | W | 2-0 |
| England League 2 | 2018/11/17 15:00 | Notts County v Cheltenham | W | 0-3 |
| England EFL Trophy | 2018/11/13 19:45 | Cheltenham v Coventry | W | 2-0 |
| England FA Cup | 2018/11/10 15:00 | Ebbsfleet United v Cheltenham | D | 0-0 |
| England League 2 | 2018/11/03 15:00 | Cheltenham v Mansfield | D | 2-2 |
| England EFL Trophy | 2018/10/30 19:45 | Cheltenham v Arsenal U21 | W | 6-2 |
| England League 2 | 2018/10/27 14:00 | Cheltenham v Stevenage | L | 0-2 |
| England League 2 | 2018/10/23 18:45 | Oldham v Cheltenham | L | 2-0 |
| England League 2 | 2018/10/20 14:00 | Forest Green v Cheltenham | D | 1-1 |
| England League 2 | 2018/11/17 15:00 | Milton Keynes Dons v Macclesfield | L | 2-0 |
| England EFL Trophy | 2018/11/13 19:45 | Macclesfield v West Brom U21 | W | 2-1 |
| England FA Cup | 2018/11/10 15:00 | Maidstone Utd v Macclesfield | L | 2-1 |
| England League 2 | 2018/11/03 15:00 | Macclesfield v Bury | L | 1-4 |
| England League 2 | 2018/10/27 14:00 | Cambridge Utd v Macclesfield | L | 1-0 |
| England League 2 | 2018/10/23 18:45 | Macclesfield v Northampton | L | 0-5 |
| England League 2 | 2018/10/20 14:00 | Macclesfield v Carlisle | W | 2-1 |
| England League 2 | 2018/10/12 18:45 | Tranmere v Macclesfield | L | 1-0 |