Arsenal 5 Middlesbrough 1
Outcome: Lost
Date: 11/20/1999
Manager: Bryan Robson
Attendance: 38082
Competition: PremierLeague
Played at: Highbury
Goals:
| Goals | Time | Assists | |
| Hamilton Ricard | 67 | ||
Team
| Player | Yellow | Red | Subbed |
| Juninho | |||
| Brian Deane | |||
| Hamilton Ricard | |||
| Paul Ince | |||
| Paul Gascoigne | |||
| Colin Cooper | |||
| Gianluca Festa | |||
| Steve Vickers | |||
| Curtis Fleming | |||
| Jason Gavin | |||
| Mark Schwarzer |
Subs
| Player | Yellow | Red | Subbed |
| Andy Campbell | |||
| Robbie Stockdale |