Leeds United v Middlesbrough, 19 September 1999
| Score | 2-0 to Leeds United |
| Referee | Dermot Gallagher |
| Competition | Premier League |
| Venue | Elland Road |
| Attendance | 34,122 |
View Leeds United v Middlesbrough head to head
Goals:
| Michael Bridges | 14 |
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| Harry Kewell | 64 |
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Goals:
Starting lineup:
Goalkeeper
Nigel Martyn
Defender
Ian Harte
Defender
Danny Mills
Defender
Jonathan Woodgate
Defender/Centre back
Lucas Radebe
Midfielder
David Batty
Midfielder
Lee Bowyer
Midfielder
David Hopkin
Midfielder/Forward
Harry Kewell
Forward
Michael Bridges
Forward
Alan Smith
Starting lineup:
Goalkeeper
Mark Schwarzer
Defender
Gianluca Festa
Defender
Gary Pallister
Defender
Steve Vickers
Defender/Centre back
Colin Cooper
Midfielder
Paul Ince
Midfielder
Robbie Mustoe
Midfielder
Keith O'Neill
Midfielder
Christian Ziege
Forward
Alun Armstrong
Forward
Brian Deane
Substitutions:
| Garry Kelly for David Hopkin | 46 |
| Darren Huckerby for Michael Bridges | 53 |
Substitutions:
| Hamilton Ricard for Alun Armstrong | 72 |
Cards:
| Lee Bowyer | Y |
Cards:
| Paul Ince | Y | |
| Gianluca Festa | Y | |
| Gary Pallister | Y | |
| Christian Ziege | Y |