Tranmere Rovers v Middlesbrough, 14 December 1999
| Score | 2-1 to Tranmere Rovers |
| Referee | David Elleray |
| Competition | League Cup Quarter-final |
| Venue | Prenton Park |
| Attendance | 10,581 |
View Tranmere Rovers v Middlesbrough head to head
Goals:
| David Kelly | 39 |
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| Andy Parkinson | 71 |
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Starting lineup:
Goalkeeper
Joseph Murphy
Defender/Centre back
Dave Challinor
Defender/Centre back
Reuben Hazell
Defender/Midfielder
Gareth Roberts
Defender/Midfielder/Forward
Gary Jones
Midfielder
Nick Henry
Midfielder
Alan Mahon
Midfielder
Alan Morgan
Forward
David Kelly
Forward
Andy Parkinson
Forward
Scott Taylor
Substitutions:
| John Achterberg for Joseph Murphy | 60 |
| Graham Allen for Alan Mahon | 82 |
| Jason Koumas for Scott Taylor | 89 |
Cards:
| Alan Morgan | Y | |
| David Kelly | Y |
Goals:
| Christian Ziege | 79 |
|
Starting lineup:
Mark Schwarzer
Goalkeeper
Robbie Stockdale
Defender/Right back
Gianluca Festa
Defender
Steve Vickers
Defender
Juninho
Midfielder
Robbie Mustoe
Midfielder
Keith O'Neill
Midfielder
Phil Stamp
Midfielder
Christian Ziege
Midfielder
Brian Deane
Forward
Hamilton Ricard
Forward
Substitutions:
| Andy Campbell for Robbie Stockdale | 74 |
Cards:
| Juninho | Y | |
| Phil Stamp | Y |