Middlesbrough 2 Tottenham Hotspur 1
Outcome: Won
Date: 12/18/1999
Manager: Bryan Robson
Attendance: 33113
Competition: Premier League
Played at: Riverside Stadium
Goals:
| Goals | Time | Assists | |
| Christian Ziege | 34 | ||
| Brian Deane | 67 | ||
Team
| Player | Yellow | Red | Subbed |
| Mark Schwarzer | |||
| Gianluca Festa | |||
| Robbie Stockdale | |||
| Christian Ziege | |||
| Steve Vickers | |||
| Robbie Mustoe | |||
| Neil Maddison | |||
| Keith Oneill | |||
| Juninho | |||
| Brian Deane | |||
| Hamilton Ricard |
Subs
| Player | Yellow | Red | Subbed |
| Alun Armstrong |