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Chesterfield 24th, English Div 2 |
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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 | 23 | 14 | 5 | 4 | 34 | 16 | 18 | 1.47 | 0.69 | | 2.04 | 47 | 5 |
| Away Record | 23 | 3 | 8 | 12 | 12 | 28 | -16 | 0.52 | 1.21 | | 0.73 | 17 | 23 |
| Overall Record | 46 | 17 | 13 | 16 | 46 | 44 | 2 | 1.00 | 0.95 | | 1.39 | 64 | 9 |
| English Div 2 |
| No. | Date | Ven | Opponent | Result | HT | Attend |
| 1 | 07-Aug-99 | H | Colchester United | L | 0-1 | (0-0) | 2,930 |
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| 2 | 14-Aug-99 | A | Burnley | L | 1-2 | (0-2) | 10,615 |
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| 3 | 21-Aug-99 | H | Cambridge United | W | 4-2 | (1-1) | 2,816 |
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| 4 | 28-Aug-99 | A | Millwall | D | 1-1 | (0-0) | 6,256 |
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| 5 | 04-Sep-99 | A | Preston North End | W | 2-0 | (0-0) | 8,506 |
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| 6 | 11-Sep-99 | H | Stoke City | L | 0-2 | (0-0) | 4,285 |
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| 7 | 18-Sep-99 | A | Reading | L | 0-1 | (0-0) | 6,932 |
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| 8 | 25-Sep-99 | A | Scunthorpe United | D | 0-0 | (0-0) | 4,321 |
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| 9 | 02-Oct-99 | H | AFC Bournemouth | L | 0-1 | (0-1) | 2,775 |
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| 10 | 09-Oct-99 | H | Blackpool | D | 0-0 | (0-0) | 2,804 |
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| 11 | 16-Oct-99 | A | Wrexham | D | 1-1 | (1-0) | 2,603 |
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| 12 | 19-Oct-99 | A | Notts County | L | 0-1 | (0-0) | 4,749 |
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| 13 | 23-Oct-99 | H | Scunthorpe United | D | 1-1 | (1-0) | 3,464 |
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| 14 | 02-Nov-99 | A | Wigan Athletic | L | 0-3 | (0-1) | 4,376 |
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| 15 | 06-Nov-99 | H | Oldham Athletic | L | 0-1 | (0-1) | 2,737 |
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| 16 | 12-Nov-99 | A | Cardiff City | L | 1-2 | (0-1) | 4,863 |
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| 17 | 20-Nov-99 | H | Bristol Rovers | L | 0-1 | (0-1) | 2,875 |
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| 18 | 27-Nov-99 | H | Oxford United | D | 0-0 | (0-0) | 2,768 |
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| 19 | 03-Dec-99 | A | Colchester United | L | 0-1 | (0-0) | 3,027 |
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| 20 | 07-Dec-99 | H | Bristol City | L | 0-2 | (0-1) | 2,254 |
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| 21 | 10-Dec-99 | A | Brentford | D | 1-1 | (0-1) | 4,286 |
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| 22 | 26-Dec-99 | A | Luton Town | D | 1-1 | (0-1) | 5,870 |
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| 23 | 03-Jan-00 | A | Wycombe Wanderers | L | 0-3 | (0-1) | 5,001 |
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| 24 | 08-Jan-00 | H | Brentford | W | 1-0 | (0-0) | 2,746 |
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| 25 | 15-Jan-00 | H | Burnley | D | 1-1 | (0-1) | 4,214 |
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| 26 | 22-Jan-00 | A | Cambridge United | L | 0-2 | (0-1) | 3,819 |
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| 27 | 29-Jan-00 | H | Millwall | W | 2-0 | (1-0) | 3,198 |
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| 28 | 01-Feb-00 | H | Gillingham | D | 0-0 | (0-0) | 2,898 |
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| 29 | 05-Feb-00 | A | Bristol City | L | 0-3 | (0-2) | 8,837 |
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| 30 | 12-Feb-00 | H | Preston North End | L | 0-1 | (0-0) | 4,726 |
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| 31 | 19-Feb-00 | A | Oxford United | L | 1-2 | (0-1) | 5,146 |
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| 32 | 26-Feb-00 | H | Reading | W | 2-0 | (1-0) | 2,986 |
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| 33 | 04-Mar-00 | A | Stoke City | L | 1-5 | (0-3) | 11,968 |
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| 34 | 11-Mar-00 | H | Wigan Athletic | D | 1-1 | (1-0) | 3,106 |
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| 35 | 18-Mar-00 | A | Bristol Rovers | L | 1-3 | (1-1) | 8,765 |
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| 36 | 21-Mar-00 | H | Cardiff City | D | 1-1 | (1-1) | 2,348 |
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| 37 | 25-Mar-00 | H | Luton Town | L | 1-3 | (0-3) | 2,597 |
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| 38 | 28-Mar-00 | H | Bury | L | 0-1 | (0-1) | 1,903 |
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| 39 | 01-Apr-00 | A | Gillingham | L | 0-1 | (0-0) | 6,772 |
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| 40 | 08-Apr-00 | H | Wycombe Wanderers | L | 1-2 | (1-0) | 2,081 |
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| 41 | 15-Apr-00 | A | Bury | D | 1-1 | (0-1) | 3,021 |
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| 42 | 18-Apr-00 | A | Oldham Athletic | W | 2-1 | (2-1) | 4,012 |
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| 43 | 22-Apr-00 | H | Wrexham | L | 0-3 | (0-1) | 2,550 |
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| 44 | 25-Apr-00 | A | AFC Bournemouth | D | 1-1 | (1-0) | 3,481 |
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| 45 | 29-Apr-00 | H | Notts County | W | 2-1 | (0-1) | 2,455 |
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| 46 | 06-May-00 | A | Blackpool | D | 2-2 | (0-1) | 3,860 |
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| English FA Cup |
| Round | Date | Ven | Opponent | Result | HT | Attend |
| 1 | 30-Oct-99 | H | Enfield Town | L | 1-2 | (0-1) | 2,506 |
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| English League Cup |
| Round | Date | Ven | Opponent | Result | HT | Attend |
| 1 L1 | 10-Aug-99 | A | Rochdale | W | 2-1 | (0-1) | 1,910 |
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| 1 L2 | 24-Aug-99 | H | Rochdale | W | 2-1 | (1-1) | 2,067 |
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| 2 L1 | 14-Sep-99 | H | Middlesbrough | D | 0-0 | (0-0) | 4,941 |
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| 2 L2 | 21-Sep-99 | A | Middlesbrough | L | 1-2 | (0-1) | 25,602 |
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| Pld | W | D | L | F | A | GD | GFA | GAA | | PpG | Pts | Rank |
| August | 4 | 1 | 1 | 2 | 6 | 6 | 0 | 1.50 | 1.50 | | 1.00 | 4 | 18 |
| September | 4 | 1 | 1 | 2 | 2 | 3 | -1 | 0.50 | 0.75 | | 1.00 | 4 | 17 |
| October | 5 | 0 | 3 | 2 | 2 | 4 | -2 | 0.40 | 0.80 | | 0.60 | 3 | 19 |
| November | 5 | 0 | 1 | 4 | 1 | 7 | -6 | 0.20 | 1.40 | | 0.20 | 1 | 24 |
| December | 4 | 0 | 2 | 2 | 2 | 5 | -3 | 0.50 | 1.25 | | 0.50 | 2 | 22 |
| January | 5 | 2 | 1 | 2 | 4 | 6 | -2 | 0.80 | 1.20 | | 1.40 | 7 | 8 |
| February | 5 | 1 | 1 | 3 | 3 | 6 | -3 | 0.60 | 1.20 | | 0.80 | 4 | 19 |
| March | 6 | 0 | 2 | 4 | 5 | 14 | -9 | 0.83 | 2.33 | | 0.33 | 2 | 24 |
| April | 7 | 2 | 2 | 3 | 7 | 10 | -3 | 1.00 | 1.42 | | 1.14 | 8 | 16 |
| May | 1 | 0 | 1 | 0 | 2 | 2 | 0 | 2.00 | 2.00 | | 1.00 | 1 | 12 |
Home and away results against each team, listed in the current league table standings
| Home | 1998-1999 | Team | 1998-1999 | Away | Pts |
| L 0-1 | [0-1] | Preston North End | [0-2] | W 2-0 | 3 |
| D 1-1 | [1-0] | Burnley | [2-1] | L 1-2 | 1 |
| D 0-0 | [1-0] | Gillingham | [1-3] | L 0-1 | 1 |
| D 1-1 | [1-1] | Wigan Athletic | [1-3] | L 0-3 | 1 |
| W 2-0 | [2-1] | Millwall | [0-0] | D 1-1 | 4 |
| L 0-2 | [1-1] | Stoke City | [0-0] | L 1-5 | 0 |
| L 0-1 | [0-0] | Bristol Rovers | [0-0] | L 1-3 | 0 |
| W 2-1 | [3-0] | Notts County | [0-2] | L 0-1 | 3 |
| L 0-2 | - | Bristol City | - | L 0-3 | 0 |
| W 2-0 | [1-0] | Reading | [2-1] | L 0-1 | 3 |
| L 0-3 | [2-1] | Wrexham | [0-0] | D 1-1 | 1 |
| L 1-2 | [2-0] | Wycombe Wanderers | [0-1] | L 0-3 | 0 |
| L 1-3 | [3-1] | Luton Town | [0-1] | D 1-1 | 1 |
| L 0-1 | [1-3] | Oldham Athletic | [0-2] | W 2-1 | 3 |
| L 0-1 | - | Bury | - | D 1-1 | 1 |
| L 0-1 | [3-1] | AFC Bournemouth | [0-0] | D 1-1 | 1 |
| W 1-0 | - | Brentford | - | D 1-1 | 4 |
| L 0-1 | [3-1] | Colchester United | [0-1] | L 0-1 | 0 |
| W 4-2 | - | Cambridge United | - | L 0-2 | 3 |
| D 0-0 | - | Oxford United | - | L 1-2 | 1 |
| D 1-1 | - | Cardiff City | - | L 1-2 | 1 |
| D 0-0 | [1-2] | Blackpool | [1-1] | D 2-2 | 2 |
| D 1-1 | - | Scunthorpe United | - | D 0-0 | 2 |
| | Chesterfield | | |
| Leading Scorers |
League Cup |
| Reeves | | 16 | |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |
| Williams | | 5 | |  |  |  |  |  |
| Willis | | 4 | |  |  |  |  |
| Payne | | 3 | |  |  |  |
| Beaumont | | 2 | |  |  |
| Howard | | 2 | |  |  |
| Breckin | | 1 | |  |
| Carss | | 1 | |  |
| Ebdon | | 1 | |  |
| Galloway | | 1 | |  |
| Lomas | | 1 | |  |
| Wilkinson | | 1 | |  |
| (own goals) | | 2 | |  |  |
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 | 5 |
| 0 | 4 | 10 | 3 | 4 |
| 1 | 1 | 10 | 4 | 2 | | 1 |
| 2 | 3 | 2 | 1 |
| 3 |
| 4 | | | 1 |
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 | 0 | 1 | 2 |
| 0 | 1 |
| 1 | | | 2 |
| 2 | | 2 |
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When the goals have been scored and conceded this season
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