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){kind=small} |
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
19 October 1999 |
| Deportivo La Coruña |
3–1 | Montpellier |
|---|---|---|
Pauleta  17'Djalminha 51' (pen.)Makaay 53' |
Report | Delaye 6' |
21 October 1999 |
| Leeds United |
4–1 | Lokomotiv Moscow |
|---|---|---|
| Bowyer 27', 45' Smith 56'Kewell 83' |
Report | Loskov 80' |
Second leg
Bologna won 4–2 on aggregate.
2–2 on aggregate. AEK Athens won on away goals rule.
Wolfsburg won 1–0 on aggregate.
Udinese won 2–1 on aggregate.
Parma won 4–1 on aggregate.
4 November 1999 |
| 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 won 4–2 on aggregate.
Roma won 3–0 on aggregate.
Celta Vigo won 4–2 on aggregate.
Deportivo La Coruña won 5–1 on aggregate.
Monaco won 3–1 on aggregate.
4 November 1999 |
| 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.
4 November 1999 |
| Nantes |
4–0 | Inter Bratislava |
|---|---|---|
| Sibierski 49' Monterrubio 61'Devineau 74'Da Rocha 82' |
Report |
Nantes won 7–0 on aggregate.
4 November 1999 |
| Amica Wronki |
1–4 | Atlético Madrid |
|---|---|---|
| Jackiewicz 34' |
Report | Hasselbaink 31' Capdevila 45'Baraja 52'Correa 84' |
Atlético Madrid won 5–1 on aggregate.
2–2 on aggregate. Panathinaikos won away goals rule.
Leeds United won 7–1 on aggregate.
Ajax won 3–1 on aggregate.
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 won 2–1 on aggregate.