Middlesbrough v Southampton, 11 September 1999
| Score | 3-2 to Middlesbrough |
| Referee | Steve Lodge |
| Competition | Premier League |
| Venue | Riverside Stadium |
| Attendance | 32,157 |
View Middlesbrough v Southampton head to head
Goals:
| Gary Pallister | 17 |
|
|
| Paul Gascoigne | penalty | 67 |
|
| Brian Deane | 78 |
|
Starting lineup:
Goalkeeper
Mark Schwarzer
Defender
Gary Pallister
Defender
Steve Vickers
Defender/Centre back
Colin Cooper
Midfielder
Paul Gascoigne
Midfielder
Paul Ince
Midfielder
Robbie Mustoe
Midfielder
Phil Stamp
Midfielder
Christian Ziege
Forward
Brian Deane
Forward
Hamilton Ricard
Substitutions:
| Alun Armstrong for Hamilton Ricard | 64 |
| Robbie Stockdale for Phil Stamp | 64 |
| Jason Gavin for Steve Vickers | 64 |
Cards:
| Hamilton Ricard | Y | |
| Colin Cooper | Y | |
| Brian Deane | Y |
Goals:
| Hassan Kachloul | 15 |
|
|
| Marian Pahars | 55 |
|
Starting lineup:
Paul Jones
Goalkeeper
Jason Dodd
Defender/Right back
Francis Benali
Defender
Claus Lundekvam
Defender
Dean Richards
Defender/Centre back
Hassan Kachloul
Midfielder
Stuart Ripley
Midfielder
Trond Egil Soltvedt
Midfielder
Luis Boa Morte
Midfielder/Forward
Mark Hughes
Forward
Marian Pahars
Forward
Substitutions:
| Matt Oakley for Stuart Ripley | 27 |
| James Beattie for Marian Pahars | 72 |
| Wayne Bridge for Hassan Kachloul | 72 |
Cards:
| Luis Boa Morte | 67 | R |