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Chelsea 5th, English Premiership |
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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 | 19 | 12 | 6 | 1 | 29 | 13 | 16 | 1.52 | 0.68 | | 2.21 | 42 | 3 |
| Away Record | 19 | 8 | 9 | 2 | 28 | 17 | 11 | 1.47 | 0.89 | | 1.73 | 33 | 2 |
| Overall Record | 38 | 20 | 15 | 3 | 57 | 30 | 27 | 1.50 | 0.78 | | 1.97 | 75 | 3 |
| English Premiership |
| No. | Date | Ven | Opponent | Result | HT | Attend |
| 1 | 07-Aug-99 | H | Sunderland | W | 4-0 | (2-0) | 34,831 |
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| 2 | 14-Aug-99 | A | Leicester City | D | 2-2 | (0-1) | 21,068 |
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| 3 | 21-Aug-99 | H | Aston Villa | W | 1-0 | (0-0) | 35,071 |
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| 4 | 28-Aug-99 | A | Wimbledon | W | 1-0 | (0-0) | 22,167 |
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| 5 | 11-Sep-99 | H | Newcastle United | W | 1-0 | (1-0) | 35,092 |
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| 6 | 18-Sep-99 | A | Watford | L | 0-1 | (0-0) | 21,244 |
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| 7 | 25-Sep-99 | A | Middlesbrough | W | 1-0 | (0-0) | 34,183 |
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| 8 | 03-Oct-99 | H | Manchester United | W | 5-0 | (2-0) | 34,909 |
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| 9 | 16-Oct-99 | A | Liverpool | L | 0-1 | (0-0) | 44,826 |
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| 10 | 23-Oct-99 | H | Arsenal | L | 2-3 | (1-0) | 34,958 |
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| 11 | 30-Oct-99 | A | Derby County | L | 1-3 | (1-1) | 28,614 |
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| 12 | 07-Nov-99 | H | West Ham United | D | 0-0 | (0-0) | 34,935 |
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| 13 | 20-Nov-99 | A | Everton | D | 1-1 | (0-1) | 38,225 |
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| 14 | 28-Nov-99 | H | Bradford City | W | 1-0 | (1-0) | 31,591 |
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| 15 | 04-Dec-99 | A | Sunderland | L | 1-4 | (0-4) | 41,377 |
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| 16 | 19-Dec-99 | H | Leeds United | L | 0-2 | (0-0) | 35,106 |
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| 17 | 26-Dec-99 | A | Southampton | W | 2-1 | (2-0) | 15,232 |
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| 18 | 29-Dec-99 | H | Sheffield Wednesday | W | 3-0 | (2-0) | 32,938 |
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| 19 | 04-Jan-00 | A | Coventry City | D | 2-2 | (0-0) | 20,164 |
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| 20 | 08-Jan-00 | A | Bradford City | D | 1-1 | (0-1) | 18,276 |
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| 21 | 12-Jan-00 | H | Tottenham Hotspur | W | 1-0 | (0-0) | 34,969 |
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| 22 | 15-Jan-00 | H | Leicester City | D | 1-1 | (0-1) | 35,063 |
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| 23 | 22-Jan-00 | A | Aston Villa | D | 0-0 | (0-0) | 33,704 |
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| 24 | 05-Feb-00 | A | Tottenham Hotspur | W | 1-0 | (0-0) | 36,041 |
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| 25 | 12-Feb-00 | H | Wimbledon | W | 3-1 | (0-0) | 34,826 |
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| 26 | 26-Feb-00 | H | Watford | W | 2-1 | (1-1) | 34,928 |
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| 27 | 04-Mar-00 | A | Newcastle United | W | 1-0 | (1-0) | 36,448 |
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| 28 | 11-Mar-00 | H | Everton | D | 1-1 | (1-0) | 35,113 |
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| 29 | 18-Mar-00 | A | West Ham United | D | 0-0 | (0-0) | 26,041 |
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| 30 | 25-Mar-00 | H | Southampton | D | 1-1 | (0-0) | 34,956 |
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| 31 | 01-Apr-00 | A | Leeds United | W | 1-0 | (0-0) | 40,162 |
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| 32 | 12-Apr-00 | H | Coventry City | W | 2-1 | (0-1) | 34,316 |
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| 33 | 15-Apr-00 | A | Sheffield Wednesday | L | 0-1 | (0-0) | 21,743 |
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| 34 | 22-Apr-00 | H | Middlesbrough | D | 1-1 | (1-1) | 34,467 |
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| 35 | 24-Apr-00 | A | Manchester United | L | 2-3 | (2-2) | 61,593 |
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| 36 | 29-Apr-00 | H | Liverpool | W | 2-0 | (2-0) | 34,957 |
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| 37 | 06-May-00 | A | Arsenal | L | 1-2 | (0-1) | 38,119 |
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| 38 | 14-May-00 | H | Derby County | W | 4-0 | (0-0) | 35,084 |
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| English FA Cup |
| Round | Date | Ven | Opponent | Result | HT | Attend |
| 3 | 11-Dec-99 | A | Hull City | W | 6-1 | (2-1) | 10,279 |
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| 4 | 19-Jan-00 | H | Nottingham Forest | W | 2-0 | (0-0) | 30,125 |
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| 5 | 30-Jan-00 | H | Leicester City | W | 2-1 | (1-0) | 30,141 |
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| QF | 20-Feb-00 | H | Gillingham | W | 5-0 | (1-0) | 34,205 |
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| SF | 09-Apr-00 | N | Newcastle United | W | 2-1 | (1-0) | 73,876 |
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| F | 20-May-00 | N | Aston Villa | W | 1-0 | (0-0) | 78,217 |
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| English League Cup |
| Round | Date | Ven | Opponent | Result | HT | Attend |
| 3 | 13-Oct-99 | H | Huddersfield Town | L | 0-1 | (0-0) | 21,008 |
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| UEFA Champions League |
| Round | Date | Ven | Opponent | Result | HT | Attend |
| Q3 L1 | 11-Aug-99 | H | Skonto Riga | W | 3-0 | (0-0) | 22,043 |
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| Q3 L2 | 25-Aug-99 | A | Skonto Riga | D | 0-0 | (0-0) | 5,023 |
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| Round 1 Gp H | 15-Sep-99 | H | AC Milan | D | 0-0 | (0-0) | 33,873 |
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| Round 1 Gp H | 21-Sep-99 | A | Hertha Berlin | L | 1-2 | (0-1) | 55,541 |
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| Round 1 Gp H | 28-Sep-99 | H | Galatasaray | W | 1-0 | (0-0) | 33,462 |
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| Round 1 Gp H | 20-Oct-99 | A | Galatasaray | W | 5-0 | (1-0) | 20,600 |
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| Round 1 Gp H | 26-Oct-99 | A | AC Milan | D | 1-1 | (0-0) | 74,855 |
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| Round 1 Gp H | 03-Nov-99 | H | Hertha Berlin | W | 2-0 | (2-0) | 33,623 |
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| Round 2 Gp D | 24-Nov-99 | H | Feyenoord | W | 3-1 | (1-0) | 29,704 |
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| Round 2 Gp D | 07-Dec-99 | A | Lazio | D | 0-0 | (0-0) | 64,500 |
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| Round 2 Gp D | 29-Feb-00 | A | Marseille | L | 0-1 | (0-1) | 24,700 |
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| Round 2 Gp D | 08-Mar-00 | H | Marseille | W | 1-0 | (1-0) | 33,206 |
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| Round 2 Gp D | 14-Mar-00 | A | Feyenoord | W | 3-1 | (1-0) | 45,000 |
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| Round 2 Gp D | 22-Mar-00 | H | Lazio | L | 1-2 | (1-0) | 34,260 |
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| QF L1 | 05-Apr-00 | H | Barcelona | W | 3-1 | (3-0) | 33,662 |
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| QF L2 | 18-Apr-00 | A | Barcelona | L | 1-5 | (0-2) | 98,000 |
| [aet] |
Home and away results against each team, listed in the current league table standings
| Home | 1998-1999 | Team | 1998-1999 | Away | Pts |
| W 5-0 | [0-0] | Manchester United | [1-1] | L 2-3 | 3 |
| L 2-3 | [0-0] | Arsenal | [0-1] | L 1-2 | 0 |
| L 0-2 | [1-0] | Leeds United | [0-0] | W 1-0 | 3 |
| W 2-0 | [2-1] | Liverpool | [1-1] | L 0-1 | 3 |
| | Chelsea | | |
| W 1-0 | [2-1] | Aston Villa | [3-0] | D 0-0 | 4 |
| W 4-0 | - | Sunderland | - | L 1-4 | 3 |
| D 1-1 | [2-2] | Leicester City | [4-2] | D 2-2 | 2 |
| D 0-0 | [0-1] | West Ham United | [1-1] | D 0-0 | 2 |
| W 1-0 | [2-0] | Tottenham Hotspur | [2-2] | W 1-0 | 6 |
| W 1-0 | [1-1] | Newcastle United | [1-0] | W 1-0 | 6 |
| D 1-1 | [2-0] | Middlesbrough | [0-0] | W 1-0 | 4 |
| D 1-1 | [3-1] | Everton | [0-0] | D 1-1 | 2 |
| W 2-1 | [2-1] | Coventry City | [1-2] | D 2-2 | 4 |
| D 1-1 | [1-0] | Southampton | [2-0] | W 2-1 | 4 |
| W 4-0 | [2-1] | Derby County | [2-2] | L 1-3 | 3 |
| W 1-0 | - | Bradford City | - | D 1-1 | 4 |
| W 3-1 | [3-0] | Wimbledon | [2-1] | W 1-0 | 6 |
| W 3-0 | [1-1] | Sheffield Wednesday | [0-0] | L 0-1 | 3 |
| W 2-1 | - | Watford | - | L 0-1 | 3 |
| Leading Scorers |
League Cup Europe |
| Flo | | 19 | |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |
| Poyet | | 18 | |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |
| Wise | | 10 | |  |  |  |  |  |  |  |  |  |  |
| Zola | | 8 | |  |  |  |  |  |  |  |  |
| Petrescu | | 5 | |  |  |  |  |  |
| Weah | | 5 | |  |  |  |  |  |
| Di Matteo | | 4 | |  |  |  |  |
| Leboeuf | | 4 | |  |  |  |  |
| Morris | | 4 | |  |  |  |  |
| Sutton | | 3 | |  |  |  |
| Babayaro | | 2 | |  |  |
| Harley | | 2 | |  |  |
| Lambourde | | 2 | |  |  |
| Ambrosetti | | 1 | |  |
| Desailly | | 1 | |  |
| Deschamps | | 1 | |  |
| Ferrer | | 1 | |  |
| Terry | | 1 | |  |
| (own goals) | | 5 | |  |  |  |  |  |
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 | Europe |
 | 0 | 1 | 2 | 3 | 4 |
| 0 | 3 | 3 | 1 |
| 1 | 9 | 6 | 1 | 1 | 1 |
| 2 | 1 | 3 | 2 | 2 |
| 3 | 1 | 1 |
| 4 | 2 |
| 5 | 1 |
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 | 0 | 1 |
| 0 | | 1 |
| 1 | 1 |
| 2 | 1 | 2 |
| 3 |
| 4 |
| 5 | 1 |
| 6 | | 1 |
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 | 0 | 1 | 2 | 3 | 4 | 5 |
| 0 | 3 | 1 |
| 1 | 2 | 1 | 2 | | | 1 |
| 2 | 1 |
| 3 | 1 | 3 |
| 4 |
| 5 | 1 |
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When the goals have been scored and conceded this season
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