1999–2000 UEFA Cup second round
The second round of the 1999–2000 UEFA Cup began on 19 October 1999. The round included 48 winners from the first round.
Matches
    
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg | 
|---|---|---|---|---|
| Aris  | 2–4 |  Celta Vigo | 2–2 | 0–2 | 
| Udinese  | 2–1 |  Legia Warsaw | 1–0 | 1–1 | 
| Deportivo La Coruña  | 5–1 |  Montpellier | 3–1 | 2–0 | 
| Widzew Łódź  | 1–3 |  Monaco | 1–1 | 0–2 | 
| MTK Hungária  | 2–2 (a) |  AEK Athens | 2–1 | 0–1 | 
| Roda  | 0–1 |  Wolfsburg | 0–0 | 0–1 | 
| Anderlecht .svg.png.webp) | 2–4 |  Bologna | 2–1 | 0–3 | 
| PAOK  | 3–3 (1–4 p) |  Benfica | 1–2 | 2–1 (a.e.t.) | 
| Inter Bratislava  | 0–7 |  Nantes | 0–3 | 0–4 | 
| Atlético Madrid  | 5–1 |  Amica Wronki | 1–0 | 4–1 | 
| Parma  | 4–1 |  Helsingborg | 1–0 | 3–1 | 
| Grazer AK  | 2–2 (a) |  Panathinaikos | 2–1 | 0–1 | 
| Steaua București  | 2–0 |  West Ham United | 2–0 | 0–0 | 
| Levski Sofia  | 2–4 |  Juventus | 1–3 | 1–1 | 
| Leeds United  | 7–1 |  Lokomotiv Moscow | 4–1 | 3–0 | 
| Hapoel Haifa  | 1–3 |  Ajax | 0–3 | 1–0 | 
| Slavia Prague  | 3–2 |  Grasshopper | 3–1 | 0–1 | 
| Zürich  | 2–5 |  Newcastle United | 1–2 | 1–3 | 
| Werder Bremen  | 2–2 (a) |  Viking | 0–0 | 2–2 | 
| Teplice  | 1–5 |  Mallorca | 1–2 | 0–3 | 
| IFK Göteborg  | 0–3 |  Roma | 0–2 | 0–1 | 
| Lyon  | 2–0 |  Celtic | 1–0 | 1–0 | 
| Lens  | 5–2 |  Vitesse | 4–1 | 1–1 | 
| Tottenham Hotspur  | 1–2 |  Kaiserslautern | 1–0 | 0–2 | 
First leg
    
| Aris  | 2–2 |  Celta Vigo | 
|---|---|---|
| Paulo Andrioli  44' Kyzeridis  68' | Report | Karpin  41', 42' | 
| Udinese  | 1–0 |  Legia Warsaw | 
|---|---|---|
| Sosa  29' | Report | 
| Deportivo La Coruña  | 3–1 |  Montpellier | 
|---|---|---|
| Pauleta  17' Djalminha  51' (pen.) Makaay  53' | Report | Delaye  6' | 
| Anderlecht .svg.png.webp) | 2–1 |  Bologna | 
|---|---|---|
| Koller  17', 35' | Report | Signori  90' | 
| Grazer AK  | 2–1 |  Panathinaikos | 
|---|---|---|
| Lipa  57' Pamić  80' | Report | Sypniewski  64' | 
| Steaua București  | 2–0 |  West Ham United | 
|---|---|---|
| Rosu  39' Ilie  56' | Report | 
| Parma  | 1–0 |  Helsingborg | 
|---|---|---|
| F. Cannavaro  44' | Report | 
| Slavia Prague  | 3–1 |  Grasshopper | 
|---|---|---|
| Ulich  19', 50' Kuchař  40' | Report | Yakin  23' | 
| Widzew Łódź  | 1–1 |  Monaco | 
|---|---|---|
| Wichniarek  5' (pen.) | Report | Giuly  40' | 
| IFK Göteborg  | 0–2 |  Roma | 
|---|---|---|
| Report | Montella  37', 52' | 
| MTK Budapest  | 2–1 |  AEK Athens | 
|---|---|---|
| Egressy  20' Erős  34' | Report | Ćirić  66' | 
| PAOK  | 1–2 |  Benfica | 
|---|---|---|
| Frantzeskos  90' | Report | Nuno Gomes  68' Ronaldo Guiaro  90' | 
| Atlético Madrid  | 1–0 |  Amica Wronki | 
|---|---|---|
| Baraja  79' | Report | 
| Leeds United  | 4–1 |  Lokomotiv Moscow | 
|---|---|---|
| Bowyer  27', 45' Smith  56' Kewell  83' | Report | Loskov  80' | 
| Tottenham Hotspur  | 1–0 |  Kaiserslautern | 
|---|---|---|
| Iversen  33' | Report | 
Second leg
    
Bologna won 4–2 on aggregate.
| AEK Athens  | 1–0 |  MTK Budapest | 
|---|---|---|
| Ćirić  75' (pen.) | Report | 
2–2 on aggregate. AEK Athens won on away goals rule.
Wolfsburg won 1–0 on aggregate.
| Legia Warsaw  | 1–1 |  Udinese | 
|---|---|---|
| Czereszewski  11' | Report | Sosa  41' | 
Udinese won 2–1 on aggregate.
| Helsingborg  | 1–3 |  Parma | 
|---|---|---|
| Stavrum  86' | Report | Di Vaio  11', 42', 43' | 
Parma won 4–1 on aggregate.
| Newcastle United  | 3–1 |  Zürich | 
|---|---|---|
| Silvio Marić  33' Ferguson  58' Speed  61' | Report | Jamarauli  17' | 
Newcastle United won 5–2 on aggregate.
Steaua București won 2–0 on aggregate.
| Juventus  | 1–1 |  Levski Sofia | 
|---|---|---|
| Kovačević  79' | Report | Atanasov  15' | 
Juventus won 4–2 on aggregate.
| Roma  | 1–0 |  IFK Göteborg | 
|---|---|---|
| Fábio Júnior  88' | Report | 
Roma won 3–0 on aggregate.
| Celta Vigo  | 2–0 |  Aris | 
|---|---|---|
| Đorović  67' Turdó  90' | Report | 
Celta Vigo won 4–2 on aggregate.
| Montpellier  | 0–2 |  Deportivo La Coruña | 
|---|---|---|
| Report | Makaay  45' Pauleta  82' | 
Deportivo La Coruña won 5–1 on aggregate.
| Monaco  | 2–0 |  Widzew Łódź | 
|---|---|---|
| Lamouchi  50' Trezeguet  84' | Report | 
Monaco won 3–1 on aggregate.
| Benfica  | 1–2 (a.e.t.) |  PAOK | 
|---|---|---|
| Kandaurov  50' | Report | Marangos  28' Sabry  44' | 
| Penalties | ||
| Ronaldo Guiaro  Maniche  Chano  Paulo Madeira  | 4–1 |  Frousos  Machairidis  Bandović | 
3–3 on aggregate. Benfica won 4–1 on penalties.
| Nantes  | 4–0 |  Inter Bratislava | 
|---|---|---|
| Sibierski  49' Monterrubio  61' Devineau  74' Da Rocha  82' | Report | 
Nantes won 7–0 on aggregate.
| Amica Wronki  | 1–4 |  Atlético Madrid | 
|---|---|---|
| Jackiewicz  34' | Report | Hasselbaink  31' Capdevila  45' Baraja  52' Correa  84' | 
Atlético Madrid won 5–1 on aggregate.
| Panathinaikos  | 1–0 |  Grazer AK | 
|---|---|---|
| Pflipsen  90' | Report | 
2–2 on aggregate. Panathinaikos won away goals rule.
| Lokomotiv Moscow  | 0–3 |  Leeds United | 
|---|---|---|
| Report | Harte  15' Bridges  28', 45' | 
Leeds United won 7–1 on aggregate.
| Ajax  | 0–1 |  Hapoel Haifa | 
|---|---|---|
| Report | Roso  60' | 
Ajax won 3–1 on aggregate.
| Grasshopper  | 1–0 |  Slavia Prague | 
|---|---|---|
| Yakin  76' | Report | 
Slavia Prague won 3–2 on aggregate.
2–2 on aggregate. Werder Bremen won on away goals rule.
Mallorca won 5–1 on aggregate.
Lyon won 2–0 on aggregate.
Lens won 5–2 on aggregate.
| Kaiserslautern  | 2–0 |  Tottenham Hotspur | 
|---|---|---|
| Buck  89' Carr  90' (o.g.) | Report | 
Kaiserslautern won 2–1 on aggregate.