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The first round of the 2000–01 UEFA Cup began on 14 September 2000. The round included 41 winners from the qualifying round, 16 losing teams from the Champions League 3rd qualifying round, 3 winners of the Intertoto Cup and 36 new entrants. This round narrowed the clubs from 96 to 48 teams for the second round.
1 This match was played at Prater Stadium in Vienna instead of Red Star's home ground in Belgrade due to UEFA deciding to accommodate Leicester City's request in which the English club claimed that "travelling to FR Yugoslavia poses a security risk due to the political situation in the country". UEFA's decision was revealed on 12 September 2000—only nine days before the match's originally scheduled date (21 September 2000). The sudden decision to not only move the tie to a neutral location but to also postpone it for a week was a highly controversial precedent since no other club drawn to travel to FR Yugoslavia for matches in European competition that season received a similar advantage: Viljandi Tulevik, Sliema Wanderers, Dynamo Kyiv, Porto, OFI, and Celta Vigo.
First leg
Antalyaspor  | 2–0 |  Werder Bremen |
|---|---|---|
Gaudino  43'Birlik 67' |
Report |
Zimbru Chişinău  | 1–2 | Hertha BSC |
|---|---|---|
| Epureanu 1' |
Report | Preetz 11' Daei 64' |
Lokomotiv Moscow  | 4–2 |  Naftex Burgas |
|---|---|---|
| Sarkisyan 23' Tsymbalar 32'Janashia 62'Pimenov 64' |
Report | Petrov 10' Timnev 54' |
IFK Norrköping  | 2–2 |  Slovan Liberec |
|---|---|---|
| Flodström 33' Andersson 79' |
Report | Lázzaro 70' Nezmar 77' |
Rapid București  | 0–1 |  Liverpool |
|---|---|---|
| Report | Barmby 29' |
Attendance: 9,782
Referee: Nicolai Vollquartz (Denmark)
Vorskla Poltava  | 1–2 |  Boavista |
|---|---|---|
| Melaschenko 38' |
Report | Couto 50' Whelliton 89' |
Ruch Chorzów  | 0–3 |  Internazionale |
|---|---|---|
| Report | Seedorf 62' Recoba 66'Keane 71' |
Celta Vigo  | 0–0 |  Rijeka |
|---|---|---|
| Report |
| Leicester City | 1–1 |  Red Star Belgrade |
|---|---|---|
| Taggart 43' |
Report | Ačimovič 2' |
Roda  | 0–2 |  Inter Bratislava |
|---|---|---|
| Report | Németh 22' Babnič 69' |
| Slavia Prague | 3–0 |  AB |
|---|---|---|
| Kuchař 30', 74' Došek 53' |
Report |
Rapid Wien  | 3–0 | Örgryte IS |
|---|---|---|
| Wagner 20' Savićević 27'Ratajczyk 79' |
Report |
Gent  | 0–6 | Ajax |
|---|---|---|
| Report | Arveladze 16' Knopper 40', 69'Grønkjær 70'van der Vaart 80'van der Gun 84' |
Lillestrøm  | 3–1 | Dynamo Moscow |
|---|---|---|
| Kristinsson 8', 13' Kihlberg 68' |
Report | Romaschenko 42' |
| CSKA Sofia | 1–2 |  MTK Budapest |
|---|---|---|
| Yanev 7' |
Report | Ferenczi 50' Kuttor 70' |
| Tirol Innsbruck | 3–1 | Fiorentina |
|---|---|---|
| Gilewicz 28', 49' Baur 45' (pen.) |
Report | Mijatović 53' |
| Club Brugge | 2–0 |  APOEL |
|---|---|---|
| Simons 37' Mendoza 63' |
Report |
| CSKA Moscow | 0–0 | Viborg |
|---|---|---|
| Report |
Celtic  | 2–0 |  HJK Helsinki |
|---|---|---|
| Larsson 14', 25' |
Report |
| Chelsea | 1–0 |  St. Gallen |
|---|---|---|
| Panucci 25' |
Report |
| Molde FK | 0–1 | Rayo Vallecano |
|---|---|---|
| Report | Bolo 16' |
HIT Gorica  | 1–4 | Roma |
|---|---|---|
| Žlogar 29' |
Report | Delvecchio 17', 19', 49' Samuel 41' |
| Vitesse Arnhem | 3–0 |  Maccabi Haifa |
|---|---|---|
| Martel 19' Peeters 63'Amoah 90' |
Report |
| Vasas | 2–2 |  AEK Athens |
|---|---|---|
| Pető 89' Komódi 90' |
Report | Pető 47' (og) Nikolaidis 50' |
| Alania Vladikavkaz | 0–3 | Amica Wronki |
|---|---|---|
| Report | Kryszałowicz 45' Król 49'Zieńczuk 89' |
| Halmstads BK | 2–1 | Benfica |
|---|---|---|
| Svensson 35' Selaković 57' |
Report | van Hooijdonk 40' |
| Polonia Warsaw | 0–1 | Udinese |
|---|---|---|
| Report | Warley 56' |
| Slovan Bratislava | 0–3 | Dinamo Zagreb |
|---|---|---|
| Report | Mujčin 38' Cvitanović 61'Pilipović 90' |
Second leg
| Hertha BSC | 2–0 | Zimbru Chişinău |
|---|---|---|
| Hartmann 23' Daei 26' |
Report |
Hertha BSC won 4–1 on aggregate.
Werder Bremen won 6–2 on aggregate.
| 1. FC Kaiserslautern | 0–1 |  Bohemians |
|---|---|---|
| Report | Crowe 37' |
1. FC Kaiserslautern won 3–2 on aggregate.
| Heart of Midlothian | 3–2 | VfB Stuttgart |
|---|---|---|
| Naysmith 17' Petrić 61'Cameron 83' |
Report | Hosny 38' Bordon 58' |
3–3 on aggregate; VfB Stuttgart won on away goals.
| 1860 München | 1–0 | Drnovice |
|---|---|---|
| Kurz 74' |
Report |
1860 München win 1–0 on aggregate.
Lokomotiv Moscow win 4–2 on aggregate.
| Slovan Liberec | 2–1 | IFK Norrköping |
|---|---|---|
| Jun 62' Nezmar 64' |
Report | Bjurström 55' |
Slovan Liberec win 4–3 on aggregate.
Liverpool won 1–0 on aggregate.
Genk won 4–1 on aggregate.
| Espanyol | 2–0 | Olimpija Ljubljana |
|---|---|---|
| Posse 15' Manel 26' |
Report |
Espanyol won 3–2 on aggregate.
Boavista won 4–2 on aggregate.
Osijek won 2–1 on aggregate.
| Internazionale | 4–1 | Ruch Chorzów |
|---|---|---|
| Recoba 6' Seedorf 41', 87'Colombo 89' |
Report | Skwara 85' |
Internazionale won 7–1 on aggregate.
Parma won 6–0 on aggregate.
| Torpedo Moscow | 0–2 | Lausanne |
|---|---|---|
| Report | Kuźba 29' Puce 62' |
Lausanne won 5–2 on aggregate.
| Rijeka | 0–1 (a.e.t.) | Celta Vigo |
|---|---|---|
| Report | Đorović 112' |
Celta Vigo won 1–0 on aggregate.
| Red Star Belgrade | 3–1 | Leicester City |
|---|---|---|
| Drulić 22', 71' Gvozdenović 47' |
Report | Izzet 41' |
Red Star Belgrade won 4–2 on aggregate.
Inter Bratislava won 4–1 on aggregate.
Nantes won 6–0 on aggregate.
| Beitar Jerusalem | 3–3 | PAOK |
|---|---|---|
| Sivilia 44', 61' Abukasis 54' (pen) |
Report | Katsabis 15' Nalitzis 42'Konstantinidis 90' |
PAOK won 6–4 on aggregate.
| AB | 0–2 | Slavia Prague |
|---|---|---|
| Report | Dostálek 46' Došek 90' |
Slavia Prague won 5–0 on aggregate.
| Örgryte IS | 1–1 | Rapid Wien |
|---|---|---|
| Johansson 73' |
Report | Wagner 60' |
Rapid Wien won 4–1 on aggregate.
| Ajax | 3–0 | Gent |
|---|---|---|
| Van der Gun 27', 58' Van der Vaart 85' |
Report |
Ajax won 9–0 on aggregate.
| Dynamo Moscow | 2–1 | Lillestrøm |
|---|---|---|
| Romaschenko 25' Shtanyuk 44' |
Report | Sundgot 71' |
Lillestrøm won 4–3 on aggregate.
GAK won 3–2 on aggregate.
| MTK Budapest | 0–1 | CSKA Sofia |
|---|---|---|
| Report | Mirchev 85' (p) |
2–2 on aggregate; MTK Budapest won on away goals.
Alavés won 4–3 on aggregate.
| Fiorentina | 2–2 | Tirol Innsbruck |
|---|---|---|
| Mijatović 22' Leandro Amaral 62' |
Report | Mair 18' Gilewicz 88' |
Tirol Innsbruck won 5–3 on aggregate.
| APOEL | 0–1 | Club Brugge |
|---|---|---|
| Report | Mendoza 30' |
Club Brugge won 3–0 on aggregate.
| Viborg | 1–0 (a.e.t.) | CSKA Moscow |
|---|---|---|
| Kærgaard 100' |
Report |
Viborg won 1–0 on aggregate.
Celtic won 3–2 on aggregate.
| Iraklis | 1–0 |  Gueugnon |
|---|---|---|
| Konstantinou 77' |
Report |
Iraklis won 1–0 on aggregate.
| St. Gallen | 2–0 | Chelsea |
|---|---|---|
| Müller 19' Amoah 35' |
Report |
St. Gallen won 2–1 on aggregate.
| Wisła Kraków | 4–1 (a.e.t.) | Zaragoza |
|---|---|---|
| Iheanacho 51' Frankowski 55', 58'Moskal 61' |
Report | Baszczyński 6' (og) |
| Penalties | ||
Żurawski  Zajac Głowacki Baszczyński  Frankowski |
4–3 | Aragón Acuña Juanele Yordi José Ignacio |
5–5 on aggregate, Wisła Kraków won 4–3 on penalties.
Rayo Vallecano won 2–1 on aggregate.
| Roma | 7–0 | HIT Gorica |
|---|---|---|
| Samuel 8' Montella 11', 19'Delvecchio 23'Totti 41', 47'Batistuta 66' |
Report |
Roma won 11–1 on aggregate.
Herfølge won 2–1 on aggregate.
| Maccabi Haifa | 2–1 | Vitesse Arnhem |
|---|---|---|
| Jano 68' Atar 88' |
Report | Amoah 90' |
Vitesse won 4–2 on aggregate.
| AEK Athens | 2–0 | Vasas |
|---|---|---|
| Maladenis 27' Nikolaidis 30' |
Report |
AEK Athens won 4–2 on aggregate.
Porto won 2–1 on aggregate.
| Amica Wronki | 2–0 | Alania Vladikavkaz |
|---|---|---|
| Kryszałowicz 37' Sobociński 73' |
Report |
Amica Wronki won 5–0 on aggregate.
| Benfica | 2–2 | Halmstads BK |
|---|---|---|
| van Hooijdonk 24' Miguel 90' |
Report | Gustafson 32' Selaković 88' |
Halmstad won 4–3 on aggregate.
Feyenoord won 4–1 on aggregate.
Bordeaux won 5–1 on aggregate.
| Udinese | 2–0 | Polonia Warsaw |
|---|---|---|
| Walem 32' Muzzi 89' |
Report |
Udinese won 3–0 on aggregate.
Basel won 7–6 on aggregate.
| OFI Crete | 6–0 | Napredak Kruševac |
|---|---|---|
| Mauro 14', 45' Gómez 25' (p), 50' (p)Iordanidis 23'Digozis 36' |
Report |
OFI Crete won 6–0 on aggregate.
| Dinamo Zagreb | 1–1 | Slovan Bratislava |
|---|---|---|
| Mujčin 70' |
Report | Sedlák 5' |
Dinamo Zagreb won 4–1 on aggregate.
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