Manchester United 1 Middlesbrough 0
Outcome: Lost
Date: 5/9/1999
Manager: Bryan Robson
Attendance: 34655
Competition: PremierLeague
Played at: Riverside Stadium
Goals:
| Goals | Time | Assists |
Team
| Player | Yellow | Red | Subbed |
| Brian Deane | |||
| Hamilton Ricard | |||
| Robbie Mustoe | |||
| Mark Summerbell | |||
| Andy Townsend | |||
| Dean Gordon | |||
| Robbie Stockdale | |||
| Gary Pallister | |||
| Steve Vickers | |||
| Jason Gavin | |||
| Mark Schwarzer |
Subs
| Player | Yellow | Red | Subbed |
| Andy Campbell | |||
| Steve Baker |