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Cheltenham Town 1st, English Conference |
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| English Conference |
| No. | Date | Ven | Opponent | Result | HT | Attend |
| 1 | 15-Aug-98 | A | Welling United | L | 1-2 | (1-1) | 820 |
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| 2 | 18-Aug-98 | H | Hednesford Town | D | 0-0 | (0-0) | 2,168 |
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| 3 | 22-Aug-98 | H | Hayes | D | 3-3 | (0-2) | 1,879 |
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| 4 | 26-Aug-98 | A | Forest Green Rovers | W | 2-1 | (0-0) | 1,909 |
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| 5 | 29-Aug-98 | A | Leek Town | W | 2-0 | (1-0) | 704 |
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| 6 | 31-Aug-98 | H | Barrow | W | 4-1 | (2-1) | 2,005 |
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| 7 | 05-Sep-98 | H | Morecambe | W | 4-1 | (2-1) | 1,959 |
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| 8 | 08-Sep-98 | A | Kettering Town | W | 2-0 | (1-0) | 1,615 |
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| 9 | 12-Sep-98 | A | Kingstonian | W | 2-1 | (1-0) | 1,801 |
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| 10 | 19-Sep-98 | H | Southport | W | 3-0 | (3-0) | 2,594 |
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| 11 | 22-Sep-98 | H | Woking | D | 1-1 | (0-1) | 2,406 |
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| 12 | 26-Sep-98 | A | Farnborough Town | W | 4-2 | (2-1) | 1,067 |
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| 13 | 03-Oct-98 | H | Dover Athletic | D | 1-1 | (0-0) | 2,575 |
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| 14 | 10-Oct-98 | A | Yeovil Town | D | 2-2 | (2-1) | 2,955 |
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| 15 | 24-Oct-98 | H | Doncaster Rovers | W | 2-1 | (2-1) | 2,428 |
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| 16 | 07-Nov-98 | A | Woking | L | 0-1 | (0-0) | 2,738 |
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| 17 | 28-Nov-98 | H | Rushden & Diamonds | W | 1-0 | (1-0) | 4,051 |
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| 18 | 05-Dec-98 | A | Dover Athletic | D | 0-0 | (0-0) | 972 |
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| 19 | 12-Dec-98 | H | Leek Town | D | 0-0 | (0-0) | 1,912 |
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| 20 | 19-Dec-98 | H | Stevenage Borough | W | 3-0 | (2-0) | 2,772 |
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| 21 | 26-Dec-98 | A | Telford United | W | 3-0 | (0-0) | 1,304 |
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| 22 | 28-Dec-98 | A | Kidderminster Harriers | W | 1-0 | (1-0) | 3,295 |
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| 23 | 02-Jan-99 | H | Telford United | W | 2-0 | (1-0) | 3,027 |
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| 24 | 09-Jan-99 | A | Doncaster Rovers | D | 2-2 | (2-0) | 3,082 |
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| 25 | 23-Jan-99 | H | Northwich Victoria | L | 0-1 | (0-1) | 2,460 |
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| 26 | 30-Jan-99 | A | Southport | W | 2-0 | (1-0) | 1,224 |
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| 27 | 13-Feb-99 | A | Morecambe | W | 2-0 | (1-0) | 1,354 |
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| 28 | 20-Feb-99 | A | Hereford United | W | 2-0 | (1-0) | 3,480 |
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| 29 | 06-Mar-99 | A | Barrow | D | 1-1 | (0-1) | 1,773 |
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| 30 | 09-Mar-99 | H | Hereford United | D | 2-2 | (1-1) | 3,341 |
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| 31 | 13-Mar-99 | A | Stevenage Borough | D | 2-2 | (1-1) | 2,576 |
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| 32 | 16-Mar-99 | H | Farnborough Town | D | 0-0 | (0-0) | 2,265 |
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| 33 | 20-Mar-99 | H | Kettering Town | W | 3-0 | (2-0) | 5,202 |
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| 34 | 22-Mar-99 | A | Hednesford Town | L | 2-3 | (1-2) | 1,651 |
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| 35 | 03-Apr-99 | A | Rushden & Diamonds | W | 2-1 | (0-1) | 6,312 |
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| 36 | 05-Apr-99 | H | Kidderminster Harriers | W | 1-0 | (0-0) | 4,518 |
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| 37 | 13-Apr-99 | H | Kingstonian | W | 1-0 | (1-0) | 3,184 |
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| 38 | 20-Apr-99 | H | Forest Green Rovers | D | 1-1 | (1-0) | 3,058 |
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| 39 | 22-Apr-99 | H | Yeovil Town | W | 3-2 | (2-1) | 6,150 |
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| 40 | 24-Apr-99 | A | Hayes | L | 2-3 | (1-1) | 2,105 |
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| 41 | 27-Apr-99 | A | Northwich Victoria | L | 0-1 | (0-0) | 1,155 |
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| 42 | 01-May-99 | H | Welling United | D | 0-0 | (0-0) | 5,400 |
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| English FA Cup |
| Round | Date | Ven | Opponent | Result | HT | Attend |
| 1 | 14-Nov-98 | H | Lincoln City | L | 0-1 | (0-0) | 3,589 |
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Home and away results against each team, listed in the current league table standings
| Home | Team | Away | Pts |
| Cheltenham Town | |
| W 3-0 | Kettering Town | W 2-0 | 6 |
| D 3-3 | Hayes | L 2-3 | 1 |
| W 1-0 | Rushden & Diamonds | W 2-1 | 6 |
| W 3-2 | Yeovil Town | D 2-2 | 4 |
| W 3-0 | Stevenage Borough | D 2-2 | 4 |
| L 0-1 | Northwich Victoria | L 0-1 | 0 |
| W 1-0 | Kingstonian | W 2-1 | 6 |
| D 1-1 | Woking | L 0-1 | 1 |
| D 0-0 | Hednesford Town | L 2-3 | 1 |
| D 1-1 | Dover Athletic | D 0-0 | 2 |
| D 1-1 | Forest Green Rovers | W 2-1 | 4 |
| D 2-2 | Hereford United | W 2-0 | 4 |
| W 4-1 | Morecambe | W 2-0 | 6 |
| W 1-0 | Kidderminster Harriers | W 1-0 | 6 |
| W 2-1 | Doncaster Rovers | D 2-2 | 4 |
| W 2-0 | Telford United | W 3-0 | 6 |
| W 3-0 | Southport | W 2-0 | 6 |
| W 4-1 | Barrow | D 1-1 | 4 |
| D 0-0 | Welling United | L 1-2 | 1 |
| D 0-0 | Leek Town | W 2-0 | 4 |
| D 0-0 | Farnborough Town | W 4-2 | 4 |
| Leading Scorers |
League Cup |
| Grayson | | 17 | |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |
| Eaton | | 9 | |  |  |  |  |  |  |  |  |  |
| Howells | | 6 | |  |  |  |  |  |  |
| Watkins | | 6 | |  |  |  |  |  |  |
| Freeman | | 5 | |  |  |  |  |  |
| Brough | | 4 | |  |  |  |  |
| Victory | | 4 | |  |  |  |  |
| Duff | | 3 | |  |  |  |
| Knight | | 3 | |  |  |  |
| Norton | | 3 | |  |  |  |
| Walker | | 3 | |  |  |  |
| Bailey | | 2 | |  |  |
| Banks | | 1 | |  |
| C. Walker | | 1 | |  |
| Smith | | 1 | |  |
| (own goals) | | 3 | |  |  |  |
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 | 3 |
| 1 | 4 | 4 | 1 |
| 2 | 6 | 4 | 4 | 2 |
| 3 | 4 | | 1 | 1 |
| 4 | | 2 | 1 |
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 | 0 | 1 |
| 0 | | 1 |
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When the goals have been scored and conceded this season