| 07 Aug 99 | r00  | ArsenalArsenal | 2 - 1 | LeicesterLeicester |
| 07 Aug 99 | r00 | ChelseaChelsea | 4 - 0 | SunderlandSunderland |
| 07 Aug 99 | r00 | CoventryCoventry | 0 - 1 | SouthamptonSouthampton |
| 07 Aug 99 | r00 | LeedsLeeds | 0 - 0 | DerbyDerby |
| 07 Aug 99 | r00 | MiddlesbroughMiddlesbrough | 0 - 1 | BradfordBradford |
| 07 Aug 99 | r00 | NewcastleNewcastle | 0 - 1 | Aston VillaAston Villa |
| 07 Aug 99 | r00 | Sheffield WedsSheffield Wed | 1 - 2 | LiverpoolLiverpool |
| 07 Aug 99 | r00 | WatfordWatford | 2 - 3 | Wimbledon FCWimbledon FC |
| 07 Aug 99 | r00 | West HamWest Ham | 1 - 0 | TottenhamTottenham |
| 08 Aug 99 | r00 | EvertonEverton | 1 - 1 | Manchester UnitedManchester Un |
| 09 Aug 99 | r00 | TottenhamTottenham | 3 - 1 | NewcastleNewcastle |
| 10 Aug 99 | r00 | DerbyDerby | 1 - 2 | ArsenalArsenal |
| 10 Aug 99 | r00 | SunderlandSunderland | 2 - 0 | WatfordWatford |
| 10 Aug 99 | r00 | Wimbledon FCWimbledon FC | 2 - 3 | MiddlesbroughMiddlesbrough |
| 11 Aug 99 | r00 | Aston VillaAston Villa | 3 - 0 | EvertonEverton |
| 11 Aug 99 | r00 | LeicesterLeicester | 1 - 0 | CoventryCoventry |
| 11 Aug 99 | r00 | Manchester UnitedManchester Un | 4 - 0 | Sheffield WedsSheffield Wed |
| 11 Aug 99 | r00 | SouthamptonSouthampton | 0 - 3 | LeedsLeeds |
| 14 Aug 99 | r00 | BradfordBradford | 1 - 1 | Sheffield WedsSheffield Wed |
| 14 Aug 99 | r00 | DerbyDerby | 1 - 3 | MiddlesbroughMiddlesbrough |
| 14 Aug 99 | r00 | LeicesterLeicester | 2 - 2 | ChelseaChelsea |
| 14 Aug 99 | r00 | LiverpoolLiverpool | 0 - 1 | WatfordWatford |
| 14 Aug 99 | r00 | Manchester UnitedManchester Un | 2 - 0 | LeedsLeeds |
| 14 Aug 99 | r00 | SunderlandSunderland | 0 - 0 | ArsenalArsenal |
| 14 Aug 99 | r00 | TottenhamTottenham | 3 - 2 | EvertonEverton |
| 14 Aug 99 | r00 | Wimbledon FCWimbledon FC | 1 - 1 | CoventryCoventry |
| 15 Aug 99 | r00 | SouthamptonSouthampton | 4 - 2 | NewcastleNewcastle |
| 16 Aug 99 | r00 | Aston VillaAston Villa | 2 - 2 | West HamWest Ham |
| 21 Aug 99 | r00 | ChelseaChelsea | 1 - 0 | Aston VillaAston Villa |
| 21 Aug 99 | r00 | CoventryCoventry | 2 - 0 | DerbyDerby |
| 21 Aug 99 | r00 | EvertonEverton | 4 - 1 | SouthamptonSouthampton |
| 21 Aug 99 | r00 | LeedsLeeds | 2 - 1 | SunderlandSunderland |
| 21 Aug 99 | r00 | MiddlesbroughMiddlesbrough | 1 - 0 | LiverpoolLiverpool |
| 21 Aug 99 | r00 | NewcastleNewcastle | 3 - 3 | Wimbledon FCWimbledon FC |
| 21 Aug 99 | r00 | Sheffield WedsSheffield Wed | 1 - 2 | TottenhamTottenham |
| 21 Aug 99 | r00 | WatfordWatford | 1 - 0 | BradfordBradford |
| 21 Aug 99 | r00 | West HamWest Ham | 2 - 1 | LeicesterLeicester |
| 22 Aug 99 | r00 | ArsenalArsenal | 1 - 2 | Manchester UnitedManchester Un |
| 23 Aug 99 | r00 | LeedsLeeds | 1 - 2 | LiverpoolLiverpool |
| 24 Aug 99 | r00 | MiddlesbroughMiddlesbrough | 0 - 3 | LeicesterLeicester |
| 24 Aug 99 | r00 | WatfordWatford | 0 - 1 | Aston VillaAston Villa |
| 25 Aug 99 | r00 | ArsenalArsenal | 2 - 0 | BradfordBradford |
| 25 Aug 99 | r00 | CoventryCoventry | 1 - 2 | Manchester UnitedManchester Un |
| 25 Aug 99 | r00 | EvertonEverton | 4 - 0 | Wimbledon FCWimbledon FC |
| 25 Aug 99 | r00 | NewcastleNewcastle | 1 - 2 | SunderlandSunderland |
| 25 Aug 99 | r00 | Sheffield WedsSheffield Wed | 0 - 2 | DerbyDerby |
| 28 Aug 99 | r00 | Aston VillaAston Villa | 1 - 0 | MiddlesbroughMiddlesbrough |
| 28 Aug 99 | r00 | BradfordBradford | 0 - 3 | West HamWest Ham |
| 28 Aug 99 | r00 | DerbyDerby | 1 - 0 | EvertonEverton |
| 28 Aug 99 | r00 | LiverpoolLiverpool | 2 - 0 | ArsenalArsenal |
| 28 Aug 99 | r00 | SouthamptonSouthampton | 2 - 0 | Sheffield WedsSheffield Wed |
| 28 Aug 99 | r00 | TottenhamTottenham | 1 - 2 | LeedsLeeds |
| 28 Aug 99 | r00 | Wimbledon FCWimbledon FC | 0 - 1 | ChelseaChelsea |
| 29 Aug 99 | r00 | SunderlandSunderland | 1 - 1 | CoventryCoventry |
| 30 Aug 99 | r00 | LeicesterLeicester | 1 - 0 | WatfordWatford |
| 30 Aug 99 | r00 | Manchester UnitedManchester Un | 5 - 1 | NewcastleNewcastle |
| 11 Sep 99 | r00 | ArsenalArsenal | 3 - 1 | Aston VillaAston Villa |
| 11 Sep 99 | r00 | ChelseaChelsea | 1 - 0 | NewcastleNewcastle |
| 11 Sep 99 | r00 | CoventryCoventry | 3 - 4 | LeedsLeeds |
| 11 Sep 99 | r00 | LiverpoolLiverpool | 2 - 3 | Manchester UnitedManchester Un |
| 11 Sep 99 | r00 | MiddlesbroughMiddlesbrough | 3 - 2 | SouthamptonSouthampton |
| 11 Sep 99 | r00 | Sheffield WedsSheffield Wed | 0 - 2 | EvertonEverton |
| 11 Sep 99 | r00 | SunderlandSunderland | 2 - 0 | LeicesterLeicester |
| 11 Sep 99 | r00 | West HamWest Ham | 1 - 0 | WatfordWatford |
| 11 Sep 99 | r00 | Wimbledon FCWimbledon FC | 2 - 2 | DerbyDerby |
| 12 Sep 99 | r00 | BradfordBradford | 1 - 1 | TottenhamTottenham |
| 18 Sep 99 | r00 | Aston VillaAston Villa | 1 - 0 | BradfordBradford |
| 18 Sep 99 | r00 | DerbyDerby | 0 - 5 | SunderlandSunderland |
| 18 Sep 99 | r00 | LeicesterLeicester | 2 - 2 | LiverpoolLiverpool |
| 18 Sep 99 | r00 | Manchester UnitedManchester Un | 1 - 1 | Wimbledon FCWimbledon FC |
| 18 Sep 99 | r00 | SouthamptonSouthampton | 0 - 1 | ArsenalArsenal |
| 18 Sep 99 | r00 | WatfordWatford | 1 - 0 | ChelseaChelsea |
| 19 Sep 99 | r00 | EvertonEverton | 1 - 0 | West HamWest Ham |
| 19 Sep 99 | r00 | LeedsLeeds | 2 - 0 | MiddlesbroughMiddlesbrough |
| 19 Sep 99 | r00 | NewcastleNewcastle | 8 - 0 | Sheffield WedsSheffield Wed |
| 19 Sep 99 | r00 | TottenhamTottenham | 3 - 2 | CoventryCoventry |
| 25 Sep 99 | r00 | ArsenalArsenal | 1 - 0 | WatfordWatford |
| 25 Sep 99 | r00 | CoventryCoventry | 1 - 0 | West HamWest Ham |
| 25 Sep 99 | r00 | DerbyDerby | 0 - 1 | BradfordBradford |
| 25 Sep 99 | r00 | LeedsLeeds | 3 - 2 | NewcastleNewcastle |
| 25 Sep 99 | r00 | LeicesterLeicester | 3 - 1 | Aston VillaAston Villa |
| 25 Sep 99 | r00 | Manchester UnitedManchester Un | 3 - 3 | SouthamptonSouthampton |
| 25 Sep 99 | r00 | MiddlesbroughMiddlesbrough | 0 - 1 | ChelseaChelsea |
| 25 Sep 99 | r00 | SunderlandSunderland | 1 - 0 | Sheffield WedsSheffield Wed |
| 26 Sep 99 | r00 | Wimbledon FCWimbledon FC | 1 - 1 | TottenhamTottenham |
| 27 Sep 99 | r00 | LiverpoolLiverpool | 0 - 1 | EvertonEverton |
| 02 Oct 99 | r00 | Aston VillaAston Villa | 0 - 0 | LiverpoolLiverpool |
| 02 Oct 99 | r00 | BradfordBradford | 0 - 4 | SunderlandSunderland |
| 02 Oct 99 | r00 | EvertonEverton | 1 - 1 | CoventryCoventry |
| 02 Oct 99 | r00 | Sheffield WedsSheffield Wed | 5 - 1 | Wimbledon FCWimbledon FC |
| 03 Oct 99 | r00 | ChelseaChelsea | 5 - 0 | Manchester UnitedManchester Un |
| 03 Oct 99 | r00 | NewcastleNewcastle | 2 - 1 | MiddlesbroughMiddlesbrough |
| 03 Oct 99 | r00 | TottenhamTottenham | 2 - 3 | LeicesterLeicester |
| 03 Oct 99 | r00 | WatfordWatford | 1 - 2 | LeedsLeeds |
| 03 Oct 99 | r00 | West HamWest Ham | 2 - 1 | ArsenalArsenal |
| 04 Oct 99 | r00 | SouthamptonSouthampton | 3 - 3 | DerbyDerby |
| 16 Oct 99 | r00 | ArsenalArsenal | 4 - 1 | EvertonEverton |
| 16 Oct 99 | r00 | CoventryCoventry | 4 - 1 | NewcastleNewcastle |
| 16 Oct 99 | r00 | DerbyDerby | 0 - 1 | TottenhamTottenham |
| 16 Oct 99 | r00 | LeedsLeeds | 2 - 0 | Sheffield WedsSheffield Wed |
Team 1999-2000 Schedules
Arsenal
Aston Villa
Bournemouth
Brentford
Brighton and Hove Albion
Chelsea
Coventry City
Crystal Palace
Everton
Fulham
Hull City
Ipswich Town
Leeds United
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Manchester City
Manchester United
Newcastle United
Nottingham Forest
Sunderland
Tottenham Hotspur
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