| 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 |
| 1999-05-08 | East FifevClydeLeague One · Scotland | 2–1 | League One · Scotland |
| 1999-05-01 | AlloavEast FifeLeague One · Scotland | 3–1 | League One · Scotland |
| 1999-04-24 | East FifevArbroathLeague One · Scotland | 1–2 | League One · Scotland |
| 1999-04-17 | East FifevForfarLeague One · Scotland | 2–1 | League One · Scotland |
| 1999-04-10 | PartickvEast FifeLeague One · Scotland | 2–2 | League One · Scotland |
| 1999-04-03 | Queen of SthvEast FifeLeague One · Scotland | 2–0 | League One · Scotland |
| 1999-03-20 | East FifevStirlingLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-03-13 | Inverness CvEast FifeLeague One · Scotland | 4–0 | League One · Scotland |
| 1999-03-06 | East FifevLivingstonLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-02-27 | East FifevAlloaLeague One · Scotland | 0–4 | League One · Scotland |
| 1999-02-20 | ClydevEast FifeLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-02-16 | ForfarvEast FifeLeague One · Scotland | 2–4 | League One · Scotland |
| 1999-02-06 | East FifevPartickLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-01-30 | StirlingvEast FifeLeague One · Scotland | 0–1 | League One · Scotland |
| 1999-01-20 | LivingstonvEast FifeLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-01-17 | East FifevQueen of SthLeague One · Scotland | 0–1 | League One · Scotland |