Tottenham Hotspur v Zimbru Chisinau, 16 September 1999
| Score | 3-0 to Tottenham Hotspur |
| Referee | Emanuel Raphael Zammit |
| Competition | UEFA Cup 1st round 1st leg |
| Venue | White Hart Lane |
| Attendance | 32,660 |
View Tottenham Hotspur v Zimbru Chisinau head to head
Goals:
| Øyvind Leonhardsen | 3 |
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| Chris Perry | 32 |
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| Tim Sherwood | 56 |
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Starting lineup:
Goalkeeper
Ian Walker
Defender
Stephen Carr
Defender
Luke Young
Defender/Centre back
Chris Perry
Defender/Left back
Mauricio Taricco
Midfielder
Steffen Freund
Midfielder
David Ginola
Midfielder
Øyvind Leonhardsen
Midfielder
Tim Sherwood
Forward
Chris Armstrong
Forward
Steffen Iversen
Substitutions:
| José Dominguez for Chris Armstrong | 76 |
| Justin Edinburgh for Mauricio Taricco | 82 |
0 Zimbru Chisinau
Goals:
Starting lineup:
Denis Romanenco
Goalkeeper
Valeriu Catînsus
Defender
Sergei Dodul
Defender
Sergei Iepureanu
Midfielder
Kostantin Kulyk
Midfielder
Igor Oprea
Midfielder
Vadim Boreţ
Forward
Iuri Miterev
Forward
Substitutions:
| Fistican for Tropanet | 46 |
| Robu for Sergei Dodul | 46 |
| Dmitry Gusila for Iuri Miterev | 82 |