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Heart of Midlothian 3rd, Scottish Premier League |
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| League Record 1998-1999 [for the same period] |
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| Pld | W | D | L | F | A | GD | GFA | GAA | | PpG | Pts | Rank |
| Home Record | 18 | 8 | 2 | 8 | 27 | 26 | 1 | 1.50 | 1.44 | | 1.44 | 26 | 5 |
| Away Record | 18 | 3 | 7 | 8 | 17 | 24 | -7 | 0.94 | 1.33 | | 0.88 | 16 | 8 |
| Overall Record | 36 | 11 | 9 | 16 | 44 | 50 | -6 | 1.22 | 1.38 | | 1.16 | 42 | 6 |
| Scottish Premier League |
| No. | Date | Ven | Opponent | Result | HT | Attend |
| 1 | 31-Jul-99 | A | St Johnstone | W | 4-1 | (1-0) | 6,705 |
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| 2 | 07-Aug-99 | H | Rangers | L | 0-4 | (0-2) | 17,893 |
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| 3 | 14-Aug-99 | A | Hibernian | D | 1-1 | (0-1) | 16,976 |
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| 4 | 22-Aug-99 | H | Aberdeen | W | 3-0 | (1-0) | 12,803 |
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| 5 | 29-Aug-99 | A | Celtic | L | 0-4 | (0-2) | 59,307 |
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| 6 | 11-Sep-99 | H | Dundee | W | 4-0 | (1-0) | 13,378 |
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| 7 | 25-Sep-99 | A | Dundee United | W | 2-0 | (1-0) | 8,510 |
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| 8 | 16-Oct-99 | H | St Johnstone | D | 1-1 | (1-0) | 12,872 |
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| 9 | 27-Oct-99 | H | Kilmarnock | D | 2-2 | (0-0) | 12,541 |
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| 10 | 30-Oct-99 | A | Dundee | L | 0-1 | (0-1) | 6,018 |
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| 11 | 06-Nov-99 | H | Motherwell | D | 1-1 | (1-0) | 12,514 |
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| 12 | 20-Nov-99 | H | Celtic | L | 1-2 | (1-0) | 17,184 |
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| 13 | 23-Nov-99 | A | Motherwell | L | 1-2 | (0-1) | 7,858 |
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| 14 | 27-Nov-99 | A | Kilmarnock | D | 2-2 | (2-0) | 8,326 |
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| 15 | 05-Dec-99 | H | Dundee United | W | 3-0 | (1-0) | 10,598 |
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| 16 | 08-Dec-99 | A | Aberdeen | L | 1-3 | (1-1) | 10,274 |
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| 17 | 19-Dec-99 | H | Hibernian | L | 0-3 | (0-2) | 17,954 |
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| 18 | 22-Dec-99 | A | Rangers | L | 0-1 | (0-0) | 49,907 |
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| 19 | 22-Jan-00 | H | Dundee | W | 2-0 | (1-0) | 13,112 |
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| 20 | 05-Feb-00 | A | Celtic | W | 3-2 | (1-2) | 59,896 |
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| 21 | 26-Feb-00 | H | Kilmarnock | D | 0-0 | (0-0) | 14,243 |
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| 22 | 01-Mar-00 | A | Motherwell | W | 2-0 | (1-0) | 5,588 |
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| 23 | 04-Mar-00 | A | Dundee United | W | 1-0 | (0-0) | 6,928 |
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| 24 | 15-Mar-00 | A | St Johnstone | W | 1-0 | (0-0) | 4,668 |
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| 25 | 18-Mar-00 | A | Hibernian | L | 1-3 | (1-1) | 15,908 |
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| 26 | 22-Mar-00 | H | Aberdeen | W | 3-0 | (1-0) | 13,249 |
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| 27 | 25-Mar-00 | H | Motherwell | D | 0-0 | (0-0) | 13,102 |
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| 28 | 01-Apr-00 | A | Dundee | D | 0-0 | (0-0) | 6,291 |
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| 29 | 08-Apr-00 | H | Celtic | W | 1-0 | (1-0) | 16,046 |
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| 30 | 12-Apr-00 | H | Rangers | L | 1-2 | (1-1) | 16,314 |
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| 31 | 15-Apr-00 | A | Aberdeen | W | 2-1 | (0-1) | 12,626 |
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| 32 | 22-Apr-00 | H | Dundee United | L | 1-2 | (0-0) | 12,604 |
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| 33 | 29-Apr-00 | A | Kilmarnock | W | 1-0 | (0-0) | 8,057 |
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| 34 | 06-May-00 | H | St Johnstone | D | 0-0 | (0-0) | 12,638 |
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| 35 | 13-May-00 | A | Rangers | L | 0-1 | (0-1) | 49,109 |
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| 36 | 21-May-00 | H | Hibernian | W | 2-1 | (1-0) | 17,391 |
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| Scottish FA Cup |
| Round | Date | Ven | Opponent | Result | HT | Attend |
| 3 | 29-Jan-00 | H | Stenhousemuir | W | 3-2 | (1-2) | 11,752 |
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| 4 | 19-Feb-00 | A | Clyde | W | 2-0 | (2-0) | 6,416 |
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| QF | 12-Mar-00 | A | Rangers | L | 1-4 | (1-2) | 31,864 |
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| Scottish League Cup |
| Round | Date | Ven | Opponent | Result | HT | Attend |
| 2 | 18-Aug-99 | A | Queen of the South | W | 3-1 | (0-1) | 5,180 |
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| 3 | 12-Oct-99 | A | East Fife | W | 2-0 | (1-0) | 3,337 |
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| QF | 02-Feb-00 | A | Kilmarnock | L | 0-1 | (0-0) | 6,648 |
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Home and away results against each team, listed in the current league table standings
| Home | 1998-1999 | Team | 1998-1999 | Away | Pts |
| L 0-4 | L 1-2 | [2-3, 2-1] | Rangers | [0-0, 0-3] | L 0-1 | L 0-1 | 0 |
| L 1-2 | W 1-0 | [2-4, 2-1] | Celtic | [0-3, 1-1] | L 0-4 | W 3-2 | 6 |
| | | Heart of Midlothian | | |
| D 1-1 | D 0-0 | [0-2, 3-0] | Motherwell | [4-0, 2-3] | L 1-2 | W 2-0 | 5 |
| D 1-1 | D 0-0 | [0-2, 1-1] | St Johnstone | [0-0, 1-1] | W 4-1 | W 1-0 | 8 |
| L 0-3 | W 2-1 | - | Hibernian | - | D 1-1 | L 1-3 | 4 |
| W 4-0 | W 2-0 | [1-2, 0-2] | Dundee | [0-2, 0-1] | L 0-1 | D 0-0 | 7 |
| W 3-0 | L 1-2 | [4-1, 0-1] | Dundee United | [3-1, 0-0] | W 2-0 | W 1-0 | 9 |
| D 2-2 | D 0-0 | [2-2, 2-1] | Kilmarnock | [0-1, 0-3] | D 2-2 | W 1-0 | 6 |
| W 3-0 | W 3-0 | [0-2, 2-0] | Aberdeen | [5-2, 0-2] | L 1-3 | W 2-1 | 9 |
| Leading Scorers |
League Cup |
| McSwegan | | 15 | |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |
| Cameron | | 11 | |  |  |  |  |  |  |  |  |  |  |  |
| Jackson | | 9 | |  |  |  |  |  |  |  |  |  |
| Wales | | 7 | |  |  |  |  |  |  |  |
| Adam | | 4 | |  |  |  |  |
| Juanjo | | 3 | |  |  |  |
| Severin | | 3 | |  |  |  |
| Flogel | | 1 | |  |
| Fulton | | 1 | |  |
| Holmes | | 1 | |  |
| Naysmith | | 1 | |  |
| Ritchie | | 1 | |  |
| (own goals) | | 1 | |  |
Score distributions by match - goals scored by row, and goals conceded by column. Each box shows the number of this season's matches with the resulting scoreline.
| League | Cup |
 | 0 | 1 | 2 | 3 | 4 |
| 0 | 4 | 3 | | 1 | 2 |
| 1 | 4 | 3 | 4 | 2 |
| 2 | 3 | 2 | 2 |
| 3 | 3 | | 1 |
| 4 | 1 | 1 |
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 | 0 | 1 | 2 | 3 | 4 |
| 0 | | 1 |
| 1 | | | | | 1 |
| 2 | 2 |
| 3 | | 1 | 1 |
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When the goals have been scored and conceded this season
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