Heart of Midlothian FC 
| 1998-08-02 | Premiership | Glasgow Rangers | (H) | 2 | - 1 | W | |
| 1998-08-16 | Premiership | Dundee United FC | (A) | 0 | - 0 | D | |
| 1998-08-22 | Premiership | Aberdeen FC | (H) | 2 | - 0 | W | |
| 1998-08-30 | Premiership | Kilmarnock FC | (A) | 0 | - 3 | L | |
| 1998-09-12 | Premiership | Dundee FC | (H) | 0 | - 2 | L | |
| 1998-09-20 | Premiership | Dunfermline Athletic | (A) | 1 | - 1 | D | |
| 1998-09-23 | Premiership | Motherwell FC | (H) | 3 | - 0 | W | |
| 1998-09-26 | Premiership | Celtic FC | (A) | 1 | - 1 | D | |
| 1998-10-04 | Premiership | St.Johnstone FC | (H) | 1 | - 1 | D | |
| 1998-10-04 | Premiership | Glasgow Rangers | (A) | 0 | - 3 | L | |
| 1998-10-24 | Premiership | Dundee United FC | (H) | 0 | - 1 | L | |
| 1998-10-31 | Premiership | Dundee FC | (A) | 0 | - 1 | L | |
| 1998-11-07 | Premiership | Kilmarnock FC | (H) | 2 | - 1 | W | |
| 1998-11-14 | Premiership | Motherwell FC | (A) | 2 | - 3 | L | |
| 1998-11-21 | Premiership | Dunfermline Athletic | (H) | 2 | - 1 | W | |
| 1998-12-06 | Premiership | Celtic FC | (H) | 2 | - 1 | W | |
| 1998-12-09 | Premiership | St.Johnstone FC | (A) | 1 | - 1 | D | |
| 1998-12-12 | Premiership | Aberdeen FC | (A) | 0 | - 2 | L | |
| 1998-12-19 | Premiership | Glasgow Rangers | (H) | 2 | - 3 | L | |
| 1998-12-26 | Premiership | Kilmarnock FC | (A) | 0 | - 1 | L | |
| 1998-12-30 | Premiership | Dundee FC | (H) | 1 | - 2 | L | |
| 1999-01-02 | Premiership | Dunfermline Athletic | (A) | 0 | - 0 | D | |
| 1999-01-30 | Premiership | Motherwell FC | (H) | 0 | - 2 | L | |
| 1999-02-06 | Premiership | Celtic FC | (A) | 0 | - 3 | L | |
| 1999-02-20 | Premiership | St.Johnstone FC | (H) | 0 | - 2 | L | |
| 1999-02-27 | Premiership | Aberdeen FC | (H) | 0 | - 2 | L | |
| 1999-03-20 | Premiership | Dundee FC | (A) | 0 | - 2 | L | |
| 1999-04-03 | Premiership | Kilmarnock FC | (H) | 2 | - 2 | D | |
| 1999-04-06 | Premiership | Dundee United FC | (A) | 3 | - 1 | W | |
| 1999-04-14 | Premiership | Celtic FC | (H) | 2 | - 4 | L | |
| 1999-04-17 | Premiership | St.Johnstone FC | (A) | 0 | - 0 | D | |
| 1999-04-24 | Premiership | Motherwell FC | (A) | 4 | - 0 | W | |
| 1999-05-03 | Premiership | Dunfermline Athletic | (H) | 2 | - 0 | W | |
| 1999-05-09 | Premiership | Glasgow Rangers | (A) | 0 | - 0 | D | |
| 1999-05-15 | Premiership | Dundee United FC | (H) | 4 | - 1 | W | |
| 1999-05-23 | Premiership | Aberdeen FC | (A) | 5 | - 2 | W |