Middlesbrough v Tottenham Hotspur, 18 December 1999
| Score | 2-1 to Middlesbrough |
| Referee | Steve Dunn |
| Competition | Premier League |
| Venue | Riverside Stadium |
| Attendance | 33,113 |
View Middlesbrough v Tottenham Hotspur head to head
Goals:
| Christian Ziege | 34 |
|
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| Brian Deane | 67 |
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Starting lineup:
Goalkeeper
Mark Schwarzer
Defender/Right back
Robbie Stockdale
Defender
Gianluca Festa
Defender
Steve Vickers
Midfielder
Juninho
Midfielder
Neil Maddison
Midfielder
Robbie Mustoe
Midfielder
Keith O'Neill
Midfielder
Christian Ziege
Forward
Brian Deane
Forward
Hamilton Ricard
Substitutions:
| Alun Armstrong for Hamilton Ricard | 85 |
| Mark Summerbell for Christian Ziege | 89 |
Cards:
| Keith O'Neill | Y | |
| Steve Vickers | Y |
Goals:
| Ramon Vega | 7 |
|
Starting lineup:
Ian Walker
Goalkeeper
Sol Campbell
Defender
Ramon Vega
Defender
Luke Young
Defender
Chris Perry
Defender/Centre back
Mauricio Taricco
Defender/Left back
Steffen Freund
Midfielder
David Ginola
Midfielder
Allan Nielsen
Midfielder
Chris Armstrong
Forward
Steffen Iversen
Forward
Substitutions:
| Tim Sherwood for Steffen Freund | 32 |
| Justin Edinburgh for David Ginola | 46 |
| Ruel Fox for Chris Armstrong | 82 |
Cards:
| Mauricio Taricco | Y | |
| Luke Young | Y | |
| David Ginola | Y | |
| Allan Nielsen | Y | |
| Allan Nielsen | Y | |
| Tim Sherwood | Y | |
| Allan Nielsen | 90 | R |