Sheffield Wednesday 1 Middlesbrough 0
Outcome: Lost
Date: 12/26/1999
Manager: Bryan Robson
Attendance: 28531
Competition: Premier League
Goals:
Team
| Player | Yellow | Red | Subbed |
| Mark Schwarzer | |||
| Curtis Fleming | |||
| Gianluca Festa | |||
| Robbie Stockdale | |||
| Steve Vickers | |||
| Neil Maddison | |||
| Phil Stamp | |||
| Robbie Mustoe | |||
| Alun Armstrong | |||
| Brian Deane | |||
| Juninho |
Subs
| Player | Yellow | Red | Subbed |
| Hamilton Ricard | |||
| Jason Gavin | |||
| Carlos Marinelli |