| 1999-10-30 | East StirlingvBrechinLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1999-10-23 | East StirlingvQueens ParkLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1999-10-16 | East FifevEast StirlingLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1999-10-02 | East StirlingvBerwickLeague Two · Scotland | 0–3 | League Two · Scotland |
| 1999-09-25 | Albion RvsvEast StirlingLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1999-09-18 | East StirlingvDumbartonLeague Two · Scotland | 1–3 | League Two · Scotland |
| 1999-09-11 | BrechinvEast StirlingLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-09-04 | MontrosevEast StirlingLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-08-28 | East StirlingvCowdenbeathLeague Two · Scotland | 0–1 | League Two · Scotland |
| 1999-08-21 | ForfarvEast StirlingLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1999-08-14 | East StirlingvEast FifeLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-08-07 | Queens ParkvEast StirlingLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1999-05-08 | East StirlingvRoss CountyLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-05-01 | BrechinvEast StirlingLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1999-04-24 | East StirlingvCowdenbeathLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1999-04-17 | Albion RvsvEast StirlingLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-04-10 | East StirlingvBerwickLeague Two · Scotland | 3–3 | League Two · Scotland |
| 1999-04-03 | Queens ParkvEast StirlingLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1999-03-20 | MontrosevEast StirlingLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1999-03-13 | East StirlingvStenhousemuirLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1999-03-06 | DumbartonvEast StirlingLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-03-02 | Ross CountyvEast StirlingLeague Two · Scotland | 4–2 | League Two · Scotland |
| 1999-02-27 | East StirlingvBrechinLeague Two · Scotland | 4–1 | League Two · Scotland |
| 1999-02-16 | East StirlingvAlbion RvsLeague Two · Scotland | 4–1 | League Two · Scotland |
| 1999-02-06 | BerwickvEast StirlingLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-01-30 | East StirlingvMontroseLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1999-01-26 | East StirlingvDumbartonLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-01-16 | East StirlingvQueens ParkLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1998-12-26 | StenhousemuirvEast StirlingLeague Two · Scotland | 2–2 | League Two · Scotland |
| 1998-12-19 | CowdenbeathvEast StirlingLeague Two · Scotland | 3–2 | League Two · Scotland |
| 1998-12-12 | East StirlingvRoss CountyLeague Two · Scotland | 2–2 | League Two · Scotland |
| 1998-11-28 | MontrosevEast StirlingLeague Two · Scotland | 2–0 | League Two · Scotland |
| 1998-11-21 | East StirlingvQueens ParkLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1998-11-14 | Albion RvsvEast StirlingLeague Two · Scotland | 3–1 | League Two · Scotland |
| 1998-11-07 | East StirlingvBerwickLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1998-10-31 | DumbartonvEast StirlingLeague Two · Scotland | 2–2 | League Two · Scotland |
| 1998-10-26 | East StirlingvStenhousemuirLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1998-10-17 | East StirlingvCowdenbeathLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1998-10-10 | BrechinvEast StirlingLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1998-10-03 | East StirlingvMontroseLeague Two · Scotland | 3–1 | League Two · Scotland |
| 1998-09-26 | Queens ParkvEast StirlingLeague Two · Scotland | 0–4 | League Two · Scotland |
| 1998-09-19 | BerwickvEast StirlingLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1998-09-12 | East StirlingvAlbion RvsLeague Two · Scotland | 0–1 | League Two · Scotland |
| 1998-09-05 | East StirlingvDumbartonLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1998-08-29 | StenhousemuirvEast StirlingLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1998-08-22 | CowdenbeathvEast StirlingLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1998-08-15 | East StirlingvBrechinLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1998-08-04 | Ross CountyvEast StirlingLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1998-05-09 | Ross CountyvEast StirlingLeague Two · Scotland | 5–2 | League Two · Scotland |
| 1998-05-02 | East StirlingvArbroathLeague Two · Scotland | 1–1 | League Two · Scotland |