Wrexham 2 Middlesbrough 1
Outcome: Lost
Date: 12/11/1999
Manager: Bryan Robson
Attendance: 11755
Competition: FACup ThirdRound
Played at: Racecourse Ground
Goals:
| Goals | Time | Assists | |
| Brian Deane | 42 | ||
Team
| Player | Yellow | Red | Subbed |
| Juninho | |||
| Brian Deane | |||
| Hamilton Ricard | |||
| Robbie Mustoe | |||
| Phil Stamp | |||
| Paul Gascoigne | |||
| Gianluca Festa | |||
| Christian Ziege | |||
| Gary Pallister | |||
| Steve Vickers | |||
| Mark Schwarzer |
Subs
| Player | Yellow | Red | Subbed |
| Jason Gavin |