1999–2000 UEFA Cup first round
The first round of the 1999–2000 UEFA Cup began on 14 September 1999. The round included 38 winners from the qualifying round, 16 losing teams from the Champions League 3rd qualifying round, 3 winners of the Intertoto Cup and 39 new entrants. This narrowed the clubs from 96, down to 48 teams in preparation for the second round.
Summary
    
Matches
    
| Steaua București  | 2–0 | |
|---|---|---|
| Ciocoiu  Dănciulescu  | 
| Red Star Belgrade  | 0–1 | |
|---|---|---|
| Loko  | 
| Montpellier  | 2–2 | |
|---|---|---|
| Ouédec  Delaye  | 
Jelić  Bošković  | 
Montpellier won 3–2 on aggregate.
| Stabæk  | 1–0 | |
|---|---|---|
| Finstad  | 
Report | 
| Deportivo La Coruña  | 2–0 | |
|---|---|---|
| Jokanović  Conceição  | 
Report | 
Deportivo La Coruña won 2–1 on aggregate.
| Partizan  | 1–3 | |
|---|---|---|
| Tomić  | 
Bowyer  Radebe  | 
| Leeds United  | 1–0 | |
|---|---|---|
| Huckerby  | 
Leeds United won 4–1 on aggregate.
| HJK Helsinki  | 0–1 | |
|---|---|---|
| Vairelles  | 
| Atlético Madrid  | 3–0 | |
|---|---|---|
| Gamarra  Hasselbaink Paunović  | 
| 1-0 | Atlético Madrid | |
|---|---|---|
| Aksancak  | 
Report | 
Atlético Madrid won 3–1 on aggregate.
| Anderlecht  | 3–0 | |
|---|---|---|
| Bajrektarevic  Radzinski  | 
| Roda JC  | 2–0 | |
|---|---|---|
| Doomernik  Zafarin  | 
Report | 
| Shakhtar Donetsk  | 1–3 | |
|---|---|---|
| Benyo  | 
Report | Tchoutang  van der Luer van Dessel  | 
Roda JC won 5–1 on aggregate.
| FK Bodø/Glimt  | 0–5 | |
|---|---|---|
| Pizarro  Bogdanović Maksymov  | 
| Viking  | 3–0 | |
|---|---|---|
| Svensson  Berre Espevoll  | 
| Sporting CP  | 1–0 | |
|---|---|---|
| Ayew  | 
Viking won 3–1 on aggregate.
| Lens  | 4–1 | |
|---|---|---|
Lens won 4–3 on aggregate.
| Kaiserslautern  | 3–0 | |
|---|---|---|
| Koch  Djorkaeff Marschall  | 
| Helsingborg  | 1–1 | |
|---|---|---|
| Jonson  | 
Report | Hetsko  | 
| Karpaty Lviv  | 1–1 | |
|---|---|---|
| Hetsko  | 
Report | Jonson  | 
| Penalties | ||
| Hetsko  Yevtushok Mizin Pavliukh  | 
2–4 | |
Helsingborg won 4–2 on penalties.
Udinese won 3–1 on aggregate.
| CSKA Sofia  | 0–2 | |
|---|---|---|
| Solano  Ketsbaia  | 
| Newcastle United  | 2–2 | |
|---|---|---|
| Shearer  Robinson  | 
Litera  Simeonov  | 
Newcastle United won 4–2 on aggregate.
| Beira-Mar  | 1–2 | |
|---|---|---|
| Faye  | 
Van Hooijdonk  Grozdić  | 
Vitesse won 2–0 on aggregate.
| Levski Sofia  | 3–0 | |
|---|---|---|
| Ivankov  Bachev Dimitrov  | 
Levski Sofia won 3–0 on aggregate.
| Celtic  | 2–0 | |
|---|---|---|
| Larsson  | 
| Hapoel Tel Aviv  | 0–1 | |
|---|---|---|
| Larsson  | 
Celtic won 3–0 on aggregate.
| Lausanne-Sports  | 3–2 | |
|---|---|---|
| Kuzba  Mazzoni  | 
Revivo  Karpin  | 
| Celta Vigo  | 4–0 | |
|---|---|---|
| McCarthy  Mostovoi  | 
Celta Vigo won 6–3 on aggregate.
| Ionikos  | 1–3 | |
|---|---|---|
  | 
Report | 
  | 
Nantes won 4–1 on aggregate.
| Roma  | 7–0 | |
|---|---|---|
| Aldair  Montella Alenichev Assunção Delvecchio  | 
| Vitória de Setúbal  | 1–0 | |
|---|---|---|
| Makinwa  | 
Roma won 7–1 on aggregate.
| Parma  | 3–2 | |
|---|---|---|
| Di Vaio  Baggio  | 
Report | Palyanytsya  Monaryov  | 
| Kryvbas Kryvyi Rih  | 0–3 | |
|---|---|---|
| Report | Boghossian  Crespo Di Vaio  | 
Parma won 6–2 on aggregate.
| Monaco  | 3–0 | |
|---|---|---|
| Simone  Trezeguet  | 
Report | 
| St Johnstone  | 3–3 | |
|---|---|---|
| Griffin  Dasovic O'Neil  | 
Report | Léonard  Pršo Legwinski  | 
Monaco won 6–3 on aggregate.
| Torpedo Kutaisi  | 0–1 | |
|---|---|---|
| Report | 
  | 
| AEK Athens  | 6–1 | |
|---|---|---|
| Report | 
  | 
AEK Athens won 7–1 on aggregate.
Juventus won 10–2 on aggregate.
West Ham United won 6–1 on aggregate.
| Benfica  | 0–1 | |
|---|---|---|
| Năstase  | 
| Dinamo București  | 0–2 | |
|---|---|---|
| Maniche  Chano  | 
Benfica won 2–1 on aggregate.
| Zenit Saint Petersburg  | 0–3 | |
|---|---|---|
| Ventola  Signori  | 
| Bologna  | 2–2 | |
|---|---|---|
| Fontolan  Cipriani  | 
Panov  Kondrashov  | 
Bologna won 5–2 on aggregate.