| 1998-12-29 | AlloavStirlingLeague One · Scotland | 2–2 | League One · Scotland |
| 1998-12-19 | LivingstonvStirlingLeague One · Scotland | 0–0 | League One · Scotland |
| 1998-12-12 | StirlingvArbroathLeague One · Scotland | 0–1 | League One · Scotland |
| 1998-11-28 | East FifevStirlingLeague One · Scotland | 2–3 | League One · Scotland |
| 1998-11-21 | StirlingvForfarLeague One · Scotland | 3–1 | League One · Scotland |
| 1998-11-14 | StirlingvPartickLeague One · Scotland | 2–0 | League One · Scotland |
| 1998-11-07 | Inverness CvStirlingLeague One · Scotland | 3–1 | League One · Scotland |
| 1998-10-31 | Queen of SthvStirlingLeague One · Scotland | 2–3 | League One · Scotland |
| 1998-10-24 | StirlingvAlloaLeague One · Scotland | 4–2 | League One · Scotland |
| 1998-10-17 | StirlingvLivingstonLeague One · Scotland | 1–3 | League One · Scotland |
| 1998-10-10 | ClydevStirlingLeague One · Scotland | 2–1 | League One · Scotland |
| 1998-10-03 | StirlingvEast FifeLeague One · Scotland | 3–2 | League One · Scotland |
| 1998-09-26 | ForfarvStirlingLeague One · Scotland | 1–2 | League One · Scotland |
| 1998-09-19 | StirlingvInverness CLeague One · Scotland | 0–1 | League One · Scotland |
| 1998-09-12 | PartickvStirlingLeague One · Scotland | 1–0 | League One · Scotland |
| 1998-09-05 | StirlingvQueen of SthLeague One · Scotland | 1–0 | League One · Scotland |
| 1998-08-29 | AlloavStirlingLeague One · Scotland | 7–0 | League One · Scotland |
| 1998-08-22 | ArbroathvStirlingLeague One · Scotland | 0–3 | League One · Scotland |
| 1998-08-15 | StirlingvClydeLeague One · Scotland | 1–2 | League One · Scotland |
| 1998-08-04 | LivingstonvStirlingLeague One · Scotland | 1–1 | League One · Scotland |
| 1998-05-09 | MortonvStirlingChampionship · Scotland | 1–0 | Championship · Scotland |
| 1998-05-02 | StirlingvSt MirrenChampionship · Scotland | 0–1 | Championship · Scotland |
| 1998-04-25 | Raith RvsvStirlingChampionship · Scotland | 0–1 | Championship · Scotland |
| 1998-04-18 | StirlingvPartickChampionship · Scotland | 0–1 | Championship · Scotland |
| 1998-04-11 | FalkirkvStirlingChampionship · Scotland | 1–0 | Championship · Scotland |
| 1998-04-04 | StirlingvAyrChampionship · Scotland | 2–0 | Championship · Scotland |
| 1998-03-28 | DundeevStirlingChampionship · Scotland | 2–0 | Championship · Scotland |
| 1998-03-21 | AirdrievStirlingChampionship · Scotland | 1–0 | Championship · Scotland |
| 1998-03-14 | StirlingvHamiltonChampionship · Scotland | 0–1 | Championship · Scotland |
| 1998-03-07 | St MirrenvStirlingChampionship · Scotland | 0–2 | Championship · Scotland |
| 1998-03-03 | HamiltonvStirlingChampionship · Scotland | 2–2 | Championship · Scotland |
| 1998-02-28 | StirlingvMortonChampionship · Scotland | 2–2 | Championship · Scotland |
| 1998-02-21 | AyrvStirlingChampionship · Scotland | 1–0 | Championship · Scotland |
| 1998-02-07 | StirlingvDundeeChampionship · Scotland | 1–3 | Championship · Scotland |
| 1998-01-31 | StirlingvAirdrieChampionship · Scotland | 2–2 | Championship · Scotland |
| 1998-01-10 | PartickvStirlingChampionship · Scotland | 1–3 | Championship · Scotland |
| 1998-01-03 | StirlingvFalkirkChampionship · Scotland | 0–6 | Championship · Scotland |