| Reserve Division Four | |||
| 04/09/1999 | Moldgreen | 0 - 5 | Aimbry |
| 11/09/1999 | H.V.Academicals | 0 - 4 | Aimbry |
| 18/09/1999 | Aimbry | 1 - 1 | Cravens |
| 25/09/1999 | Scholes 'A' | P - P | Aimbry |
| 02/10/1999 | Aimbry | 3 - 5 | New Mill 'A' |
| 09/10/1999 | Scissett 'A' | 0 - 3 | Aimbry |
| 16/10/1999 | Aimbry | 5 - 0 | Scholes 'A' |
| 23/10/1999 | Aimbry | 3 - 1 | Deanhousemuir |
| 30/10/1999 | Aimbry | 3 - 0 | Scissett 'A' |
| Gee Cup Round One | |||
| 13/11/1999 | Aimbry | 2 - 0 | New Mill 'A' |
| 20/11/1999 | Aimbry | 3 - 3 | Scapegoat Hill Utd |
| 27/11/1999 | Aimbry | P - P | Hade Edge |
| 08/01/2000 | Cravens | 3 - 1 | Aimbry |
| 22/01/2000 | Aimbry | 5 - 1 | Marsden 'A' |
| 29/01/2000 | Aimbry | 4 - 2 | H.V.Academicals |
| 05/02/2000 | Hade Edge | 0 - 3 | Aimbry |
| Gee Cup Round Two | |||
| 12/02/2000 | Scapegoat Hill Utd | 0 - 1 | Aimbry |
| 19/02/2000 | Deanhousemuir | 1 - 6 | Aimbry |
| 26/02/2000 | New Mill 'A' | 4 - 1 | Aimbry |
| 04/03/2000 | Marsden 'A' | 5 - 4 | Aimbry |
| 11/03/2000 | Aimbry | 3 - 5 | Moldgreen |
| Gee Cup Round Three Quarter Final | |||
| 18/03/2000 | BYE | P - P | Aimbry |
| 01/04/2000 | Scapegoat Hill Utd | 1 - 2 | Aimbry |
| Gee Cup Semi Final | |||
| 06/04/2000 | Aimbry | 0 - 4 | Scissett 'A' |