Tranmere Rovers 2 Middlesbrough 1
Outcome: Lost
Date: 12/14/1999
Manager: Bryan Robson
Attendance: 10581
Competition: LeagueCup FifthRound
Played at: Prenton Park
Goals:
| Goals | Time | Assists | |
| Christian Ziege | 79 | ||
Team
| Player | Yellow | Red | Subbed |
| Juninho | |||
| Brian Deane | |||
| Hamilton Ricard | |||
| Robbie Mustoe | |||
| Phil Stamp | |||
| Keith Oneill | |||
| Gianluca Festa | |||
| Robbie Stockdale | |||
| Christian Ziege | |||
| Steve Vickers | |||
| Mark Schwarzer |
Subs
| Player | Yellow | Red | Subbed |
| Andy Campbell |