| 1999-05-08 | StenhousemuirvBrechinLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1999-05-01 | CowdenbeathvStenhousemuirLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-04-24 | StenhousemuirvDumbartonLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-04-17 | MontrosevStenhousemuirLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-04-10 | StenhousemuirvRoss CountyLeague Two · Scotland | 3–2 | League Two · Scotland |
| 1999-04-03 | StenhousemuirvBerwickLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1999-03-20 | Albion RvsvStenhousemuirLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-03-13 | East StirlingvStenhousemuirLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1999-03-06 | StenhousemuirvQueens ParkLeague Two · Scotland | 4–1 | League Two · Scotland |
| 1999-02-27 | StenhousemuirvCowdenbeathLeague Two · Scotland | 4–1 | League Two · Scotland |
| 1999-02-23 | StenhousemuirvMontroseLeague Two · Scotland | 3–1 | League Two · Scotland |
| 1999-02-20 | BrechinvStenhousemuirLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-02-06 | Ross CountyvStenhousemuirLeague Two · Scotland | 2–2 | League Two · Scotland |
| 1999-01-30 | StenhousemuirvAlbion RvsLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-01-26 | Queens ParkvStenhousemuirLeague Two · Scotland | 4–1 | League Two · Scotland |
| 1999-01-16 | BerwickvStenhousemuirLeague Two · Scotland | 2–1 | League Two · Scotland |