| 1999-12-11 | BrechinvAlbion RvsLeague Two · Scotland | 8–1 | League Two · Scotland |
| 1999-12-07 | BrechinvBerwickLeague Two · Scotland | 0–3 | League Two · Scotland |
| 1999-11-27 | East FifevBrechinLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1999-11-20 | DumbartonvBrechinLeague Two · Scotland | 1–3 | League Two · Scotland |
| 1999-11-14 | BrechinvCowdenbeathLeague Two · Scotland | 2–0 | League Two · Scotland |
| 1999-11-06 | BrechinvMontroseLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1999-10-30 | East StirlingvBrechinLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1999-10-23 | BrechinvForfarLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-10-16 | Queens ParkvBrechinLeague Two · Scotland | 5–3 | League Two · Scotland |
| 1999-10-02 | BrechinvEast FifeLeague Two · Scotland | 1–3 | League Two · Scotland |
| 1999-09-25 | BerwickvBrechinLeague Two · Scotland | 2–0 | League Two · Scotland |
| 1999-09-18 | MontrosevBrechinLeague Two · Scotland | 0–1 | League Two · Scotland |
| 1999-09-11 | BrechinvEast StirlingLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-09-04 | CowdenbeathvBrechinLeague Two · Scotland | 6–1 | League Two · Scotland |
| 1999-08-28 | BrechinvDumbartonLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-08-21 | Albion RvsvBrechinLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1999-08-14 | BrechinvQueens ParkLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-08-07 | ForfarvBrechinLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1999-05-08 | StenhousemuirvBrechinLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1999-05-01 | BrechinvEast StirlingLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1999-04-24 | Queens ParkvBrechinLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-04-17 | DumbartonvBrechinLeague Two · Scotland | 2–0 | League Two · Scotland |
| 1999-04-10 | BrechinvAlbion RvsLeague Two · Scotland | 3–1 | League Two · Scotland |
| 1999-04-03 | BrechinvRoss CountyLeague Two · Scotland | 0–1 | League Two · Scotland |
| 1999-03-20 | BerwickvBrechinLeague Two · Scotland | 2–3 | League Two · Scotland |
| 1999-03-13 | MontrosevBrechinLeague Two · Scotland | 1–3 | League Two · Scotland |
| 1999-03-09 | Ross CountyvBrechinLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1999-03-06 | BrechinvCowdenbeathLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-02-27 | East StirlingvBrechinLeague Two · Scotland | 4–1 | League Two · Scotland |
| 1999-02-20 | BrechinvStenhousemuirLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-02-16 | BrechinvMontroseLeague Two · Scotland | 2–3 | League Two · Scotland |
| 1999-02-13 | BrechinvDumbartonLeague Two · Scotland | 3–3 | League Two · Scotland |
| 1999-02-06 | Albion RvsvBrechinLeague Two · Scotland | 4–1 | League Two · Scotland |
| 1999-01-30 | BrechinvBerwickLeague Two · Scotland | 0–3 | League Two · Scotland |
| 1999-01-26 | CowdenbeathvBrechinLeague Two · Scotland | 0–2 | League Two · Scotland |