| 3.12.20162016-12-3 16:00:00 | 16:00 | FA Cup | 3. R |
Formartine Utd - Annan Athletic
| 4:0 (0:0) |
| 29.10.20162016-10-29 16:00:00 | 16:00 | FA Cup | 2. R |
East Stirlingshire - Annan Athletic
| 1:2 (1:1) | Ochilview ParkGladstone RoadStenhousemuir,FK5 4QLGB |
| 22.10.20162016-10-22 16:00:00 | 16:00 | FA Cup | 2. R |
Annan Athletic - East Stirlingshire
| 0:0 (0:0) | Galabank StadiumNorth StreetAnnan,DG12 5DQGB |
| 2.8.20162016-8-2 20:45:00 | 20:45 | Challenge Cup | 1. R |
Celtic U20 - Annan Athletic
| 5:1 (3:1) | Cappielow ParkSinclair StreetGreenock,PA15 2TYGB |
| 30.7.20162016-7-30 16:00:00 | 16:00 | League Cup Grp. F | 5. R |
East Stirlingshire - Annan Athletic
| 0:2 (0:0) |
| 23.7.20162016-7-23 16:00:00 | 16:00 | League Cup Grp. F | 3. R |
Annan Athletic - Motherwell
| 1:3 (1:1) |
