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Heart of Midlothian Football Club
Scottish Premier League Fixtures 1999-00
| Date | Opposition | Venue | Result | |
| July 1999 | F | A | ||
| 21 | Fulham (Friendly) | H | 3 | 2 |
| 24 | Spurs (Friendly) | H | 2 | 2 |
| 31 | St Johnstone | A | 4 | 1 |
| August | ||||
| 18 | QOS (League Cup) | A | 3 | 1 |
| 7 | Rangers |
H | 0 | 4 |
| 14 | Hibs | A | 1 | 1 |
| 22 | Aberdeen | H | 3 | 0 |
| 29 | Celtic | A | 0 | 4 |
| September | ||||
| 11 | Dundee | H | 4 | 0 |
| 23/11/99 | Motherwell | A | ||
| 25 | Dundee United | A | 2 | 0 |
| October | ||||
| 27 th | Kilmarnock | H | 2 | 2 |
| 12th | East Fife (LC) | A | 2 | 0 |
| 16 | St Johnstone | H | 1 | 1 |
| Dec 22nd | Rangers | A | ||
| 30 | Dundee | A | ||
| November | ||||
| 6 | Motherwell | H | ||
| 13 | Aberdeen | A | ||
| 20 | Celtic | H | ||
| 27 | Kilmarnock | A | ||
| December | ||||
| 5 (6.05pm) | Dundee United | H | ||
| 11 | St Johnstone | A | ||
| 19 (6.05pm) | Hibs | H | ||
| 27 | Motherwell | A | ||
| January | ||||
| 22 | Dundee | H | ||
| February | ||||
| 5 | Celtic | A | ||
| 12 | Aberdeen | H | ||
| 26 | Kilmarnock | H | ||
| March | ||||
| 4 | Dundee united | A | ||
| 11 | Rangers | H | ||
| 18 | Hibs | A | ||
| 25 | Motherwell | H | ||
| April | ||||
| 1 | Dundee | A | ||
| 8 | Celtic | H | ||
| 15 | Aberdeen | A | ||
| 22 | Dundee United | H | ||
| 29 | Kilmarnock | A | ||
| May | ||||
| 6 | St Johnstone | H | ||
| 13 | Rangers | A | ||
| 20 | Hibs | H | ||
* All matches are liable to be changed for Sky TV coverage
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