| 1999-12-18 | PartickvStenhousemuirLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-12-04 | StenhousemuirvAlloaLeague One · Scotland | 1–3 | League One · Scotland |
| 1999-11-27 | ClydevStenhousemuirLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-11-20 | StranraervStenhousemuirLeague One · Scotland | 2–0 | League One · Scotland |
| 1999-11-10 | StenhousemuirvHamiltonLeague One · Scotland | 0–0 | League One · Scotland |
| 1999-11-06 | ArbroathvStenhousemuirLeague One · Scotland | 0–3 | League One · Scotland |
| 1999-10-30 | StenhousemuirvQueen of SthLeague One · Scotland | 2–1 | League One · Scotland |
| 1999-10-23 | StenhousemuirvPartickLeague One · Scotland | 0–1 | League One · Scotland |
| 1999-10-15 | StirlingvStenhousemuirLeague One · Scotland | 5–1 | League One · Scotland |
| 1999-10-02 | StenhousemuirvClydeLeague One · Scotland | 1–3 | League One · Scotland |
| 1999-09-25 | AlloavStenhousemuirLeague One · Scotland | 1–4 | League One · Scotland |
| 1999-09-18 | StenhousemuirvArbroathLeague One · Scotland | 1–3 | League One · Scotland |
| 1999-09-11 | Queen of SthvStenhousemuirLeague One · Scotland | 0–3 | League One · Scotland |
| 1999-09-05 | HamiltonvStenhousemuirLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-08-28 | StenhousemuirvStranraerLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-08-21 | Ross CountyvStenhousemuirLeague One · Scotland | 0–0 | League One · Scotland |
| 1999-08-14 | StenhousemuirvStirlingLeague One · Scotland | 2–1 | League One · Scotland |
| 1999-08-07 | PartickvStenhousemuirLeague One · Scotland | 0–1 | League One · Scotland |
| 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 |