Hibernian FC 
| 1999-07-31 | Premiership | Motherwell FC | (H) | 2 | - 2 | D | |
| 1999-08-08 | Premiership | Dundee FC | (A) | 4 | - 3 | W | |
| 1999-08-14 | Premiership | Heart of Midlothian FC | (H) | 1 | - 1 | D | |
| 1999-08-21 | Premiership | St.Johnstone FC | (A) | 1 | - 1 | D | |
| 1999-08-28 | Premiership | Glasgow Rangers | (H) | 0 | - 1 | L | |
| 1999-09-11 | Premiership | Dundee United FC | (A) | 1 | - 3 | L | |
| 1999-09-19 | Premiership | Kilmarnock FC | (H) | 0 | - 3 | L | |
| 1999-09-25 | Premiership | Celtic FC | (H) | 0 | - 2 | L | |
| 1999-10-02 | Premiership | Aberdeen FC | (A) | 2 | - 2 | D | |
| 1999-10-16 | Premiership | Motherwell FC | (A) | 2 | - 2 | D | |
| 1999-10-23 | Premiership | Dundee FC | (H) | 5 | - 2 | W | |
| 1999-10-31 | Premiership | Dundee United FC | (H) | 3 | - 2 | W | |
| 1999-11-06 | Premiership | Kilmarnock FC | (A) | 2 | - 0 | W | |
| 1999-11-20 | Premiership | Glasgow Rangers | (A) | 0 | - 2 | L | |
| 1999-11-24 | Premiership | St.Johnstone FC | (H) | 0 | - 1 | L | |
| 1999-11-27 | Premiership | Aberdeen FC | (H) | 2 | - 0 | W | |
| 1999-12-04 | Premiership | Celtic FC | (A) | 0 | - 4 | L | |
| 1999-12-11 | Premiership | Motherwell FC | (H) | 2 | - 2 | D | |
| 1999-12-19 | Premiership | Heart of Midlothian FC | (A) | 3 | - 0 | W | |
| 1999-12-27 | Premiership | Kilmarnock FC | (H) | 2 | - 2 | D | |
| 2000-01-22 | Premiership | Dundee United FC | (A) | 0 | - 0 | D | |
| 2000-02-06 | Premiership | Glasgow Rangers | (H) | 2 | - 2 | D | |
| 2000-02-22 | Premiership | St.Johnstone FC | (A) | 0 | - 1 | L | |
| 2000-02-26 | Premiership | Aberdeen FC | (A) | 0 | - 4 | L | |
| 2000-03-05 | Premiership | Celtic FC | (H) | 2 | - 1 | W | |
| 2000-03-18 | Premiership | Heart of Midlothian FC | (H) | 3 | - 1 | W | |
| 2000-03-21 | Premiership | Dundee FC | (H) | 1 | - 2 | L | |
| 2000-03-25 | Premiership | Kilmarnock FC | (A) | 0 | - 1 | L | |
| 2000-04-01 | Premiership | Dundee United FC | (H) | 1 | - 0 | W | |
| 2000-04-15 | Premiership | St.Johnstone FC | (H) | 3 | - 3 | D | |
| 2000-04-22 | Premiership | Celtic FC | (A) | 1 | - 1 | D | |
| 2000-04-29 | Premiership | Aberdeen FC | (H) | 1 | - 0 | W | |
| 2000-05-03 | Premiership | Glasgow Rangers | (A) | 2 | - 5 | L | |
| 2000-05-06 | Premiership | Motherwell FC | (A) | 0 | - 2 | L | |
| 2000-05-14 | Premiership | Dundee FC | (A) | 0 | - 1 | L | |
| 2000-05-21 | Premiership | Heart of Midlothian FC | (A) | 1 | - 2 | L |