| 16.11.20162016-11-16 20:45:00 | 20:45 | FA Cup | 1. R |
Brackley Town - Gillingham
| 4:3 (2:1) |
| 8.11.20162016-11-8 20:45:00 | 20:45 | EFL Trophy Southern Group H | 3. R |
West Bromwich Albion Academy - Gillingham
| 0:2 (0:1) | The HawthornsHalfords LaneWest Bromwich,B71 4LFGB |
| 5.11.20162016-11-5 16:00:00 | 16:00 | FA Cup | 1. R |
Gillingham - Brackley Town
| 2:2 (2:2) |
| 4.10.20162016-10-4 20:45:00 | 20:45 | EFL Trophy Southern Group H | 2. R |
Millwall - Gillingham
| 2:1 (1:1) | The DenZampa RoadLondon,SE16 3LNGB |
| 21.9.20162016-9-21 21:00:00 | 21:00 | EFL Cup | 3. R |
Tottenham Hotspur - Gillingham
| 5:0 (1:0) | White Hart Lane748 High RoadLondon,N17 OARGB |
| 30.8.20162016-8-30 20:30:00 | 20:30 | EFL Trophy Southern Group H | 1. R |
Gillingham - Luton Town
| 1:2 (0:2) |
