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1999-00
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| Date | Opponent | Ven | FT | HT | Scorers | Opp Scorers | Att | Pts | Pos | Booked | Sent Off |
| 15-Jul | FC Den Bosch |
(a) |
2-1 | 1-1 | McClen 27, Coppinger 50(pen) | Van der Laan 42 | 1,700 | - | - | ||
| 16-Jul | SV Deurne | (a) | 4-0 | 1-0 | Shearer
38(pen), Barton 68, McClen 76, Coppinger 85 |
1,200 | - | - | |||
| 17-Jul | Helmond Sport | (a) | 2-1 | 1-1 | Andersson
21, Ketsbaia 90 |
Vroomans 44 | 1,500 | - | - | Griffin | |
| 20-Jul | Livingston | (a) | 1-2 | 0-1 | Dyer 88 | Bingham 24, McManus 49 | 4,934 | - | - | ||
| 22-Jul | Dundee United | (a) | 1-3 | 0-2 | Robinson 84 | Dodds 7, Paterson 20, Johnsson 62 | 7,987 | - | - | ||
| 24-Jul | Reading | (a) | 2-2 | 0-2 | Coppinger 62(pen), Robinson 81 | Caskey 9, Williams 20 | 16,884 | - | - | ||
| 27-Jul | Celtic | (a) | 0-2 | 0-0 | Tebily 50 Viduka 62 | 59,252 | - | - | Speed | ||
| 28-Jul | Stoke City | (a) | 2-1 | 1-1 | Dumas 41 Robinson 67 | Jacobsen 44 | 6,742 | - | - | ||
| 31-Jul | Vfl Bochum | (a) | 2-3 | 1-1 | Shearer 38,56 | Baluszynski 41,63 Schreiber 67 | 11,644 | - | - | Speed Charvet | |
| 07-Aug | Aston Villa | (h) | 0-1 | 0-0 | Joachim 75 | 36,367 | 0 | 18 | Goma Barton Speed | Shearer | |
| 09-Aug | Tottenham |
(a) |
1-3 | 1-2 | Solano 16 | Iversen 29 Ferdinand 45 Sherwood 61 | 28,701 | 0 | 19 | Solano Speed Goma Barton Ketsbaia | |
| 15-Aug | Southampton | (a) | 2-4 | 1-0 | Shearer
22(pen) Speed 84 |
Kachloul 58,68, Pahars 66, Hughes 78 | 15,013 | 0 | 20 | ||
| 21-Aug | Wimbledon | (h) | 3-3 | 2-1 | Speed 7 Domi 28 Solano 46(pen) | Hughes 44 Ainsworth 68,90 | 35,809 | 1 | 18 | ||
| 25-Aug | Sunderland | (h) | 1-2 | 1-0 | Dyer 27 | Quinn 64 Phillips 74 | 36,600 | 1 | 19 | Domi Goma McClen | |
| 30-Aug | Man United | (a) | 1-5 | 1-1 | Berg(og) 31 | Cole 14,46,65,71 Giggs 80 | 55,190 | 1 | 19 | Barton Solano | Dabizas |
| 11-Sep | Chelsea | (a) | 0-1 | 0-1 |
Leboeuf 38(pen) |
35,092 | 1 | 19 | Solano Barton Dabizas Dyer | ||
| 16-Sep | CSKA
Sofia UEFA R1 L1 |
(a) | 2-0 | 0-0 | Solano 51 Ketsbaia 77 | 25,000 | - | - | Domi Barton Dyer | ||
| 19-Sep | Sheff Wed | (h) | 8-0 | 4-0 | Hughes 11, Shearer 30, 33(pen), 42, 81, 84(pen) Dyer 46, Speed 78 | 36,619 | 4 | 19 | |||
| 25-Sep | Leeds | (a) | 2-3 | 1-2 | Shearer 42, 54 | Bowyer 11 Kewell 39 Bridges 77 | 40,192 | 4 | 19 | Domi Marcelino Speed | |
| 30-Sep | CSKA
Sofia UEFA R1 L2 |
(h) | 2-2 | 1-1 | Shearer 36, Robinson 88 | Litera 29 Simeonov 90 | 36,228 | - | - | Shearer Speed | |
| 03-Oct | Middlesbrough | (h) | 2-1 | 2-0 | Shearer 17, 44 | Deane 89 | 36,421 | 7 | 19 | Dabizas Goma | |
| 12-Oct | Birmingham
City WC 3rd Round |
(a) | 0-2 | 0-1 | Johnson
45 (pen) Purse 60 |
19,795 | - | - | Barton, Pistone | Harper | |
| 16-Oct | Coventry City | (a) | 1-4 | 0-3 | Domi 82 | Palmer 14 Williams 22 Keane 39 Hadji 90 | 23,031 | 7 | 19 | Solano, Dabizas | Barton |
| 21-Oct | FC
Zurich UEFA R2 L1 |
(a) | 2-1 | 0-0 | Maric 51 Shearer 60 | Castillo 68 | 9,600 | - | - | Harper | |
| 25-Oct | Derby County | (h) | 2-0 | 1-0 | Eranio (og) 41 Shearer 52 | 35,614 | 10 | 17 | |||
| 30-Oct | Arsenal | (a) | 0-0 | 0-0 | 38,106 | 11 | 17 | Lee Dabizas | |||
| 04-Nov | FC
Zurich UEFA Cup R2 L2 |
(h) | 3-1 | 1-1 | Maric
33 Ferguson 58, Speed 61 |
Jamarauli 17 | 34,502 | - | - | ||
| 07-Nov | Everton | (h) | 1-1 | 0-0 | Shearer 46(pen) | Campbell 62 | 36,164 | 12 | 16 | Speed Dumas | |
| 20-Nov | Watford | (a) | 1-1 | 0-0 | Dabizas 59 | Ngonge 53 | 19,354 | 13 | 16 | Marcelino Lee | |
| 25-Nov | AS
Roma UEFA Cup R3 L1 @8.15pm |
(a) | 0-1 | 0-0 | Totti 49 | 45,655 | - | - | Shearer | ||
| 28-Nov | Tottenham | (h) | 2-1 | 1-1 | Glass 5 Dabizas 59 | Armstrong 44 | 36,460 | 16 | 15 | Solano | |
| 04-Dec | Aston Villa | (a) | 1-0 | 0-0 | Ferguson 65 | 34,531 | 19 | 14 | Pistone Speed Dabizas |
||
| 09-Dec | AS
Roma UEFA Cup R3 L2 @8.15pm |
(h) | 0-0 | 0-0 | 35,739 | - | - | Lee | |||
| 12 Dec | Tottenham FA Cup 3rd Rd | (a) | 1-1 | 0-0 | Speed 77 | Iversen 57 | 33,116 | - | - | Helder | |
| 18-Dec | Bradford | (a) | 0-2 | 0-0 | Saunders 56 Wetherall 71 | 18,276 | 19 | 15 | Helder | ||
| 22 Dec | Tottenham FA Cup 3rd Rd Rep | (h) | 6-1 | 3-1 | Speed 5 Dabizas 27 Ferguson 45, Dyer 73 Shearer 83(pen),85 | Ginola 34 | 35,415 | - | - | Lee Ferguson | |
| 26-Dec | Liverpool | (h) | 2-2 | 1-1 | Shearer 12 Ferguson 67 | Owen 31,52 | 36,445 | 20 | 15 | ||
| 28-Dec | Leicester | (a) | 2-1 | 1-0 | Ferguson
21 Shearer 53 |
Zagorakis 83 | 21,225 | 23 | 14 | ||
| 03-Jan | West Ham | (h) | 2-2 | 1-0 | Dabizas 17 Speed 65 | Lampard 84 Stimac 88 | 36,314 | 24 | 15 | ||
| 08-Jan | Sheff
United FA Cup 4th Rd |
(h) | 4-1 | 1-1 | Shearer 5 Dabizas 47 Ferguson 59 Gallacher 69 | Smith 17 | 36,220 | - | - | Speed Shearer | |
| 16-Jan | Southampton | (h) | 5-0 | 4-0 | Ferguson
3,4 Solano 17 Dryden(og) 31 Dabizas 83 |
35,623 | 27 | 13 | |||
| 22-Jan | Wimbledon | (a) | 0-2 | 0-0 | Earle 48 Gayle 69 | 22,118 | 27 | 15 | |||
| 31-Jan | Blackburn FA Cup 5th Round | (a) | 2-1 | 1-1 | Shearer 21,79 | Jansen 25 | 29,946 | - | - | Helder, Shearer | |
| 05-Feb | Sunderland | (a) | 2-2 | 2-1 | Domi 11 Helder 21 | Phillips 22,82 | 42,192 | 28 | 13 | Dabizas, Lee | |
| 12-Feb | Man United | (h) | 3-0 | 1-0 | Ferguson 26 Shearer 76,86 | 36,470 | 31 | 13 | Shearer | ||
| 20-Feb | Tranmere FA Cup Quarter- final |
(a) | 3-2 | 2-1 | Speed
27 Domi 36 Ferguson 59 |
Allison
45 Jones 76 |
15,776 | - | - | ||
| 26-Feb | Sheff Wed | (a) | 2-0 | 1-0 | Gallacher
12 Shearer 86 |
29,212 | 34 | 12 | Barton | ||
| 04-Mar | Chelsea | (h) | 0-1 | 0-1 | Poyet 22 | 36,448 | 34 | 12 | |||
| 11-Mar | Watford | (h) | 1-0 | 0-0 | Gallacher 58 | 36,433 | 37 | 12 | |||
| 19-Mar | Everton | (a) | 2-0 | 0-0 | Hughes
79 Dyer 87 |
32,512 | 40 | 11 | Speed Ferguson Howey | ||
| 25-Mar | Liverpool | (a) | 1-2 | 0-0 | Shearer 69 | Camara 52, Redknapp 89 | 44,743 | 40 | 11 | Goma | |
| 01-Apr | Bradford | (h) | 2-0 | 1-0 | Speed
7 Shearer 89 |
36,572 | 43 | 11 | |||
| 09-Apr | Chelsea FAC SF Wembley |
(n) | 1-2 | 0-1 | Lee 66 | Poyet 17,72 | 73,836 | - | - | ||
| 12-Apr | West Ham Utd | (a) | 1-2 | 0-0 | Speed 48 | Wanchope 60,89 | 25,817 | 43 | 10 | Lee Solano |
|
| 15-Apr | Leicester | (h) | 0-2 | 0-1 | Cottee
7 Savage 52 |
36,426 | 43 | 11 | |||
| 23-Apr | Leeds United | (h) | 2-2 | 1-2 | Shearer 24,48 | Bridges 12 Wilcox 17 | 36,460 | 44 | 12 | Shearer | |
| 29-Apr | Coventry City | (h) | 2-0 | 0-0 | Shearer 78(pen), Gavilan 83 | 36,408 | 47 | 12 | |||
| 02-May | Middlesbrough | (a) | 2-2 | 2-1 | Speed
10 Pistone 18 |
Juninho
5 Festa 78 |
34,744 | 48 | 12 | ||
| 06-May | Derby County | (a) | 0-0 | 0-0 | 32,724 | 49 | 12 | Lee | |||
| 14-May | Arsenal | (h) | 4-2 | 2-1 | Speed
6,59 Shearer 23 Griffin 63 |
Kanu
7, Malz 53 |
36,450 | 52 | 11 | ||
| 18-May | PFL Allstars | (a) | 1-0 | 0-0 | Gallacher 52 | 100 | - | - | |||
| 21-May | Tobago XI | (a) | 4-2 | 2-0 | Gallacher
20 Gavilan 23 Solano 67,89 |
James 55 Hutchinson 84(pen) | 4,000 | - | - |