| 2000-01-03 | CowdenbeathvEast FifeLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1999-12-04 | Queens ParkvEast FifeLeague Two · Scotland | 0–1 | League Two · Scotland |
| 1999-11-27 | East FifevBrechinLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1999-11-20 | MontrosevEast FifeLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-11-14 | East FifevAlbion RvsLeague Two · Scotland | 1–4 | League Two · Scotland |
| 1999-11-06 | East FifevCowdenbeathLeague Two · Scotland | 2–3 | League Two · Scotland |
| 1999-10-30 | ForfarvEast FifeLeague Two · Scotland | 3–2 | League Two · Scotland |
| 1999-10-23 | BerwickvEast FifeLeague Two · Scotland | 0–1 | League Two · Scotland |
| 1999-10-16 | East FifevEast StirlingLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1999-10-02 | BrechinvEast FifeLeague Two · Scotland | 1–3 | League Two · Scotland |
| 1999-09-25 | East FifevQueens ParkLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1999-09-18 | CowdenbeathvEast FifeLeague Two · Scotland | 4–0 | League Two · Scotland |
| 1999-09-11 | East FifevForfarLeague Two · Scotland | 2–0 | League Two · Scotland |
| 1999-09-04 | Albion RvsvEast FifeLeague Two · Scotland | 1–3 | League Two · Scotland |
| 1999-08-28 | East FifevMontroseLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1999-08-21 | East FifevDumbartonLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1999-08-14 | East StirlingvEast FifeLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-08-07 | East FifevBerwickLeague Two · Scotland | 1–2 | League Two · Scotland |