Middlesbrough v Arsenal, 30 November 1999
| Score | 2-2 :: penalties 3-1 to Middlesbrough |
| Referee | Mike Riley |
| Competition | League Cup 4th round |
| Venue | Riverside Stadium |
| Attendance | 23,157 |
View Middlesbrough v Arsenal head to head
Middlesbrough won 3-1 on penalties.
After extra time - 2-2 at 90 minutes.
2 (3) Middlesbrough
Goals:
| Hamilton Ricard | 8 |
|
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| Hamilton Ricard | penalty | 83 |
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Starting lineup:
Goalkeeper
Mark Schwarzer
Defender
Gianluca Festa
Defender
Curtis Fleming
Defender
Steve Vickers
Defender/Centre back
Colin Cooper
Midfielder
Paul Ince
Midfielder
Juninho
Midfielder
Keith O'Neill
Midfielder
Christian Ziege
Forward
Brian Deane
Forward
Hamilton Ricard
Substitutions:
| Phil Stamp for Keith O'Neill | 64 |
| Robbie Mustoe for Paul Ince | 110 |
| Paul Gascoigne for Brian Deane | 112 |
Cards:
| Paul Ince | Y | |
| Hamilton Ricard | Y | |
| Juninho | Y |
2 (1) Arsenal
Goals:
| Thierry Henry | 38 |
|
|
| Davor Suker | 80 |
|
Starting lineup:
Alex Manninger
Goalkeeper
Oleg Luzhny
Defender
Matthew Upson
Defender
Nelson Vivas
Defender/Full back
Sylvinho
Defender/Left back
Stefan Malz
Midfielder
Ray Parlour
Midfielder
Paolo Vernazza
Midfielder
Tommy Black
Forward
Thierry Henry
Forward
Davor Suker
Forward
Substitutions:
| Rhys Weston for Oleg Luzhny | 46 |
| Jermaine Pennant for Tommy Black | 73 |
| Ashley Cole for Ray Parlour | 89 |
Cards:
| Davor Suker | Y | |
| Nelson Vivas | Y |