Arsenal v Middlesbrough, 20 November 1999
| Score | 5-1 to Arsenal |
| Referee | Neale Barry |
| Competition | Premier League |
| Venue | Highbury |
| Attendance | 38,082 |
View Arsenal v Middlesbrough head to head
5 Arsenal
Manager: Arsene Wenger
Goals:
| Marc Overmars | 25 |
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| Dennis Bergkamp | 39 |
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| Dennis Bergkamp | 49 |
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| Marc Overmars | 61 |
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| Marc Overmars | 77 |
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Starting lineup:
Goalkeeper
David Seaman
Defender
Tony Adams
Defender
Lee Dixon
Defender/Midfielder
Gilles Grimandi
Defender/Left back
Nigel Winterburn
Midfielder
Freddie Ljungberg
Midfielder
Marc Overmars
Midfielder
Ray Parlour
Midfielder
Emmanuel Petit
Forward
Dennis Bergkamp
Forward
Nwankwo Kanu
Substitutions:
| Matthew Upson for Gilles Grimandi | 50 |
| Nelson Vivas for Lee Dixon | 71 |
| Davor Suker for Dennis Bergkamp | 75 |
Cards:
| Tony Adams | Y |
Goals:
| Hamilton Ricard | 67 |
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Starting lineup:
Mark Schwarzer
Goalkeeper
Gianluca Festa
Defender
Curtis Fleming
Defender
Steve Vickers
Defender
Colin Cooper
Defender/Centre back
Jason Gavin
Defender/Centre back
Paul Gascoigne
Midfielder
Paul Ince
Midfielder
Juninho
Midfielder
Brian Deane
Forward
Hamilton Ricard
Forward
Substitutions:
| Robbie Stockdale for Steve Vickers | 13 |
| Robbie Mustoe for Robbie Stockdale | 46 |
| Andy Campbell for Juninho | 75 |
Cards:
| Brian Deane | Y | |
| Paul Ince | Y | |
| Paul Gascoigne | Y | |
| Gianluca Festa | Y |