Tottenham Hotspur v Crewe Alexandra, 13 October 1999
| Score | 3-1 to Tottenham Hotspur |
| Referee | Clive Wilkes |
| Competition | League Cup 3rd round |
| Venue | White Hart Lane |
| Attendance | 25,486 |
View Tottenham Hotspur v Crewe Alexandra head to head
Goals:
| Øyvind Leonhardsen | 55 |
|
|
| David Ginola | 63 |
|
|
| Tim Sherwood | 88 |
|
Starting lineup:
Goalkeeper
Ian Walker
Defender
Sol Campbell
Defender
Stephen Carr
Defender/Centre back
Chris Perry
Defender/Left back
Mauricio Taricco
Midfielder
Steffen Freund
Midfielder
David Ginola
Midfielder
Øyvind Leonhardsen
Midfielder
Tim Sherwood
Midfielder/Forward
John Piercy
Forward
Chris Armstrong
Substitutions:
| Steffen Iversen for John Piercy | 74 |
Goals:
| Shaun Smith | penalty | 70 |
|
Starting lineup:
Jason Kearton
Goalkeeper
Mark Foran
Defender/Centre back
Steve Macauley
Defender/Centre back
David Wright
Defender/Midfielder
Shaun Smith
Defender/Left back
Phil Charnock
Midfielder
Kenny Lunt
Midfielder
Neil Sorvel
Midfielder
Colin Cramb
Forward
Colin Little
Forward
Mark Rivers
Forward
Substitutions:
| Kevin Street for Kenny Lunt | 33 |
| John Grant for Mark Rivers | 46 |
| James Collins for Phil Charnock | 84 |