Middlesbrough v Liverpool, 21 August 1999
| Score | 1-0 to Middlesbrough |
| Referee | Steve Dunn |
| Competition | Premier League |
| Venue | Riverside Stadium |
| Attendance | 34,783 |
View Middlesbrough v Liverpool head to head
Goals:
| Brian Deane | 49 |
|
Starting lineup:
Goalkeeper
Mark Schwarzer
Defender
Gianluca Festa
Defender
Gary Pallister
Defender
Steve Vickers
Midfielder
Paul Gascoigne
Midfielder
Paul Ince
Midfielder
Phil Stamp
Midfielder
Andy Townsend
Midfielder
Christian Ziege
Forward
Brian Deane
Forward
Hamilton Ricard
Substitutions:
| Keith O'Neill for Paul Gascoigne | 19 |
| Robbie Mustoe for Phil Stamp | 84 |
| Andy Campbell for Hamilton Ricard | 88 |
Cards:
| Phil Stamp | Y | |
| Andy Townsend | Y |
Goals:
Starting lineup:
Sander Westerveld
Goalkeeper
Jamie Carragher
Defender
Vegard Heggem
Defender
Sami Hyypiä
Defender
Steve Staunton
Defender
Dominic Matteo
Defender/Midfielder
Patrik Berger
Midfielder
Steven Gerrard
Midfielder
Jamie Redknapp
Midfielder
Titi Camara
Forward
Robbie Fowler
Forward
Substitutions:
| David Thompson for Patrik Berger | 65 |
| Erik Meijer for Steve Staunton | 71 |
Cards:
| Steven Gerrard | Y | |
| Robbie Fowler | Y | |
| Titi Camara | Y |