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Cheltenham Town 8th, English Div 3 |
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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 | 21 | 11 | 9 | 1 | 35 | 14 | 21 | 1.66 | 0.66 | | 2.00 | 42 | 1 |
| Away Record | 21 | 11 | 5 | 5 | 36 | 22 | 14 | 1.71 | 1.04 | | 1.80 | 38 | 2 |
| Overall Record | 42 | 22 | 14 | 6 | 71 | 36 | 35 | 1.69 | 0.85 | | 1.90 | 80 | 1 |
| English Div 3 |
| No. | Date | Ven | Opponent | Result | HT | Attend |
| 1 | 07-Aug-99 | H | Rochdale | L | 0-2 | (0-2) | 5,189 |
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| 2 | 14-Aug-99 | A | Mansfield Town | W | 1-0 | (0-0) | 2,348 |
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| 3 | 21-Aug-99 | H | Hull City | W | 1-0 | (1-0) | 4,427 |
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| 4 | 28-Aug-99 | A | Hartlepool United | W | 1-0 | (1-0) | 2,390 |
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| 5 | 30-Aug-99 | H | Barnet | L | 1-2 | (0-1) | 3,518 |
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| 6 | 12-Sep-99 | H | Shrewsbury Town | L | 0-1 | (0-1) | 3,704 |
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| 7 | 18-Sep-99 | A | Peterborough United | L | 0-1 | (0-0) | 5,493 |
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| 8 | 25-Sep-99 | A | Brighton & Hove Albion | L | 0-1 | (0-0) | 5,705 |
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| 9 | 02-Oct-99 | H | Rotherham United | L | 0-2 | (0-1) | 3,331 |
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| 10 | 09-Oct-99 | H | Southend United | W | 2-1 | (1-0) | 3,118 |
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| 11 | 16-Oct-99 | A | Darlington | L | 0-1 | (0-1) | 4,802 |
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| 12 | 19-Oct-99 | A | Chester City | L | 1-2 | (0-0) | 1,705 |
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| 13 | 23-Oct-99 | H | Brighton & Hove Albion | D | 0-0 | (0-0) | 4,050 |
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| 14 | 02-Nov-99 | A | Halifax Town | D | 1-1 | (0-1) | 1,956 |
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| 15 | 06-Nov-99 | H | Carlisle United | W | 3-1 | (1-1) | 3,118 |
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| 16 | 12-Nov-99 | A | Northampton Town | L | 2-3 | (1-2) | 5,837 |
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| 17 | 16-Nov-99 | A | Swansea City | D | 0-0 | (0-0) | 4,299 |
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| 18 | 23-Nov-99 | H | Plymouth Argyle | W | 2-0 | (1-0) | 5,140 |
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| 19 | 27-Nov-99 | H | Leyton Orient | W | 2-0 | (2-0) | 3,604 |
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| 20 | 04-Dec-99 | A | Rochdale | D | 0-0 | (0-0) | 2,245 |
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| 21 | 11-Dec-99 | H | Macclesfield Town | D | 1-1 | (0-0) | 3,107 |
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| 22 | 26-Dec-99 | H | Exeter City | W | 3-1 | (3-0) | 5,012 |
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| 23 | 28-Dec-99 | A | York City | W | 2-1 | (2-0) | 2,936 |
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| 24 | 03-Jan-00 | H | Lincoln City | L | 0-2 | (0-1) | 4,012 |
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| 25 | 08-Jan-00 | A | Macclesfield Town | W | 2-1 | (1-0) | 3,221 |
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| 26 | 15-Jan-00 | H | Mansfield Town | W | 1-0 | (1-0) | 3,150 |
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| 27 | 22-Jan-00 | A | Hull City | D | 1-1 | (0-1) | 4,691 |
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| 28 | 29-Jan-00 | H | Hartlepool United | W | 2-1 | (2-0) | 3,630 |
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| 29 | 05-Feb-00 | A | Barnet | L | 2-3 | (1-2) | 2,727 |
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| 30 | 13-Feb-00 | H | Swansea City | D | 0-0 | (0-0) | 4,220 |
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| 31 | 19-Feb-00 | A | Leyton Orient | L | 0-1 | (0-1) | 4,884 |
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| 32 | 26-Feb-00 | H | Peterborough United | W | 2-1 | (1-0) | 4,250 |
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| 33 | 04-Mar-00 | A | Shrewsbury Town | W | 2-0 | (1-0) | 2,876 |
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| 34 | 11-Mar-00 | H | Halifax Town | W | 3-0 | (1-0) | 3,478 |
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| 35 | 14-Mar-00 | A | Torquay United | D | 1-1 | (1-0) | 2,378 |
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| 36 | 18-Mar-00 | A | Plymouth Argyle | L | 0-1 | (0-1) | 4,392 |
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| 37 | 21-Mar-00 | H | Northampton Town | W | 2-1 | (1-0) | 4,515 |
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| 38 | 25-Mar-00 | A | Exeter City | W | 2-1 | (0-0) | 3,007 |
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| 39 | 01-Apr-00 | H | Torquay United | W | 2-0 | (1-0) | 5,128 |
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| 40 | 04-Apr-00 | A | Carlisle United | D | 1-1 | (0-0) | 2,388 |
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| 41 | 08-Apr-00 | A | Lincoln City | W | 2-1 | (2-0) | 3,133 |
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| 42 | 15-Apr-00 | H | York City | L | 0-1 | (0-0) | 4,722 |
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| 43 | 22-Apr-00 | H | Darlington | D | 0-0 | (0-0) | 5,059 |
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| 44 | 24-Apr-00 | A | Rotherham United | L | 0-2 | (0-1) | 5,447 |
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| 45 | 29-Apr-00 | H | Chester City | W | 1-0 | (0-0) | 5,391 |
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| 46 | 06-May-00 | A | Southend United | L | 1-2 | (1-1) | 4,977 |
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| English FA Cup |
| Round | Date | Ven | Opponent | Result | HT | Attend |
| 1 | 30-Oct-99 | H | Gillingham | D | 1-1 | (0-1) | 3,188 |
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| 1r | 09-Nov-99 | A | Gillingham | L | 2-3 | (0-2) | 4,352 |
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| English League Cup |
| Round | Date | Ven | Opponent | Result | HT | Attend |
| 1 L1 | 10-Aug-99 | A | Norwich City | L | 0-2 | (0-2) | 12,276 |
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| 1 L2 | 24-Aug-99 | H | Norwich City | W | 2-1 | (0-0) | 4,203 |
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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 |
| D 0-0 | - | Swansea City | - | D 0-0 | 2 |
| L 0-2 | - | Rotherham United | - | L 0-2 | 0 |
| W 2-1 | - | Northampton Town | - | L 2-3 | 3 |
| D 0-0 | - | Darlington | - | L 0-1 | 1 |
| W 2-1 | - | Peterborough United | - | L 0-1 | 3 |
| L 1-2 | - | Barnet | - | L 2-3 | 0 |
| W 2-1 | - | Hartlepool United | - | W 1-0 | 6 |
| | Cheltenham Town | | |
| W 2-0 | - | Torquay United | - | D 1-1 | 4 |
| L 0-2 | - | Rochdale | - | D 0-0 | 1 |
| D 0-0 | - | Brighton & Hove Albion | - | L 0-1 | 1 |
| W 2-0 | - | Plymouth Argyle | - | L 0-1 | 3 |
| D 1-1 | - | Macclesfield Town | - | W 2-1 | 4 |
| W 1-0 | - | Hull City | - | D 1-1 | 4 |
| L 0-2 | - | Lincoln City | - | W 2-1 | 3 |
| W 2-1 | - | Southend United | - | L 1-2 | 3 |
| W 1-0 | - | Mansfield Town | - | W 1-0 | 6 |
| W 3-0 | - | Halifax Town | - | D 1-1 | 4 |
| W 2-0 | - | Leyton Orient | - | L 0-1 | 3 |
| L 0-1 | - | York City | - | W 2-1 | 3 |
| W 3-1 | - | Exeter City | - | W 2-1 | 6 |
| L 0-1 | - | Shrewsbury Town | - | W 2-0 | 3 |
| W 3-1 | - | Carlisle United | - | D 1-1 | 4 |
| W 1-0 | - | Chester City | - | L 1-2 | 3 |
| Leading Scorers |
League Cup |
| Grayson | | 11 | |  |  |  |  |  |  |  |  |  |  |  |
| Milton | | 10 | |  |  |  |  |  |  |  |  |  |  |
| Devaney | | 6 | |  |  |  |  |  |  |
| Victory | | 5 | |  |  |  |  |  |
| McAuley | | 4 | |  |  |  |  |
| Brough | | 3 | |  |  |  |
| Howarth | | 3 | |  |  |  |
| Howells | | 3 | |  |  |  |
| Duff | | 2 | |  |  |
| Freeman | | 2 | |  |  |
| Freestone | | 2 | |  |  |
| Yates | | 2 | |  |  |
| (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 |
| 0 | 5 | 7 | 4 |
| 1 | 5 | 5 | 3 |
| 2 | 4 | 8 | | 2 |
| 3 | 1 | 2 |
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 | 0 | 1 | 2 | 3 |
| 0 | | | 1 |
| 1 | | 1 |
| 2 | | 1 | | 1 |
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When the goals have been scored and conceded this season