| Division Five | |||
| 25/08/1999 | Deanhousemuir | 5 - 2 | Thongsbridge Ath |
| 01/09/1999 | Woolpack St John | 1 - 1 | Deanhousemuir |
| 04/09/1999 | Deanhousemuir | 8 - 3 | Oakes |
| 11/09/1999 | S.G.Singh Sabha | 4 - 2 | Deanhousemuir |
| 18/09/1999 | Linthwaite Athletic | 1 - 1 | Deanhousemuir |
| 25/09/1999 | Paddock Rangers | 1 - 4 | Deanhousemuir |
| 02/10/1999 | Deanhousemuir | 2 - 0 | Brook Motors |
| Sheffield Junior Trophy Round Two | |||
| 09/10/1999 | Dodworth Miners W. | 4 - 3 | Deanhousemuir |
| FA Challenge Cup Round One | |||
| 16/10/1999 | Scissett | 3 - 1 | Deanhousemuir |
| 23/10/1999 | Deanhousemuir | 2 - 4 | Laund Hill YMCA |
| 30/10/1999 | Thongsbridge Ath | 1 - 3 | Deanhousemuir |
| 06/11/1999 | Deanhousemuir | 1 - 0 | Woolpack St John |
| Groom Cup Round One | |||
| 13/11/1999 | Black Star | 1 - 2 | Deanhousemuir |
| 20/11/1999 | Paddock Rangers | 1 - 4 | Deanhousemuir |
| 27/11/1999 | Oakes | 1 - 10 | Deanhousemuir |
| 04/12/1999 | Deanhousemuir | 8 - 2 | S.G.Singh Sabha |
| 08/01/2000 | Deanhousemuir | 5 - 0 | Oakes |
| 22/01/2000 | Brook Motors | 2 - 1 | Deanhousemuir |
| 29/01/2000 | Deanhousemuir | 2 - 2 | Moldgreen |
| 05/02/2000 | Laund Hill YMCA | 1 - 2 | Deanhousemuir |
| Groom Cup Round Two | |||
| 12/02/2000 | Deanhousemuir | 1 - 2 | H.V.Academicals |
| 19/02/2000 | Moldgreen | 2 - 3 | Deanhousemuir |
| 26/02/2000 | Deanhousemuir | 3 - 1 | Linthwaite Athletic |
| 04/03/2000 | S.G.Singh Sabha | 0 - 2 | Deanhousemuir |
| 11/03/2000 | Deanhousemuir | 2 - 6 | Linthwaite Athletic |
| 18/03/2000 | Woolpack St John | 2 - 7 | Deanhousemuir |
| 25/03/2000 | Deanhousemuir | 2 - 3 | Brook Motors |
| 01/04/2000 | Moldgreen | 1 - 0 | Deanhousemuir |
| 08/04/2000 | Deanhousemuir | 2 - 1 | Laund Hill YMCA |
| 11/04/2000 | Deanhousemuir | 12 - 1 | Thongsbridge Ath |
| 15/04/2000 | Deanhousemuir | 5 - 0 | Paddock Rangers |