Wrexham v Middlesbrough, 11 December 1999
| Score | 2-1 to Wrexham |
| Referee | Steve Lodge |
| Competition | FA Cup 3rd round |
| Venue | Racecourse Ground, Wrexham |
| Attendance | 11,755 |
View Wrexham v Middlesbrough head to head
2 Wrexham
Goals:
| Robin Gibson | 50 |
|
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| Darren Ferguson | 68 |
|
Starting lineup:
Goalkeeper
Kevin Dearden
Defender/Right back
Mark McGregor
Defender
Steve Roberts
Defender/Centre back
Brian Carey
Defender/Left back
Phil Hardy
Midfielder
Darren Ferguson
Midfielder
Robin Gibson
Midfielder
Kevin Russell
Midfielder
Danny Williams
Forward
Craig Faulconbridge
Forward
Neil Roberts
Substitutions:
| Patrick Connolly for Craig Faulconbridge | 66 |
| Gareth Owen for Robin Gibson | 72 |
| Dave Ridler for Steve Roberts | 81 |
Cards:
| Steve Roberts | Y | |
| Neil Roberts | Y |
Goals:
| Brian Deane | 42 |
|
Starting lineup:
Mark Schwarzer
Goalkeeper
Gianluca Festa
Defender
Gary Pallister
Defender
Steve Vickers
Defender
Paul Gascoigne
Midfielder
Juninho
Midfielder
Robbie Mustoe
Midfielder
Phil Stamp
Midfielder
Christian Ziege
Midfielder
Brian Deane
Forward
Hamilton Ricard
Forward
Substitutions:
| Jason Gavin for Gary Pallister | 40 |