| Tournament details | |
|---|---|
| Teams | 22 |
| Final positions | |
| Champions | Shimizu S-Pulse (1st title) |
| Runners-up | Al-Zawraa |
| Third place | Bangkok Bank |
| Fourth place | Navbahor Namangan |
← 1998–99 2000–01 → | |
The 1999–2000 Asian Cup Winners' Cup was the tenth edition of association football competition run by the Asian Football Confederation specifically for its members cup holders.
First round
West Asia
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Esteghlal | 15–0 | Homenmen | 7–0 | 8–0 |
| Al Arabi | (w/o)1 | Al-Zawraa | ||
| Al Ittihad | 1–4 | Al Rayyan | 0–2 | 1–2 |
| Al Jaish | 2–2 (a) | Al Ain | 0–1 | 2–1 |
| Kaisar Hurricane | 3–3 (4–3 p) | Khujand | 3–0 | 0–3 |
| Al Ahli | bye | |||
| Al Ittihad | bye | |||
| Navbahor Namangan | bye |
1 Al Arabi withdrew
East Asia
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| New Radiant | 1–4 | Công An Thành Phố Hồ Chí Minh | 1–3 | 0–1 |
Second round
West Asia
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Al Ittihad | 2–1 | Esteghlal | 1–0 | 1–1 |
| Al-Zawraa | 5–4 | Al Rayyan | 5–2 | 0–2 |
| Al Ahli | 3–0 | Al-Jaish | 1–0 | 2–0 |
| Kaisar Hurricane | 2–3 | Navbahor Namangan | 2–2 | 0–1 |
East Asia
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Shanghai Shenhua | 0–2 | Shimizu S-Pulse | 0–0 | 0–2 |
| Sembawang Rangers | (w/o)1 | Anyang LG Cheetahs | ||
| Công An Thành Phố Hồ Chí Minh | 1–4 | South China | 1–1 | 0–3 |
| Bangkok Bank | 6–0 | Persebaya Surabaya | 5–0 | 1–0 |
1 Sembawang Rangers withdrew before 1st leg
Quarterfinals
West Asia
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Al Ittihad | 1–2 | Al-Zawraa | 1–2 | 0–0 |
| Al Ahli | 6–31 | Navbahor Namangan | 6–1 | 0–2 |
1 Al Ahli withdrew for the semifinals, and were replaced by Navbahor Namangan; Al Ahli were banned for one year from Asian club competitions.
East Asia
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Shimizu S-Pulse | 5–2 | Anyang LG Cheetahs | 3–1 | 2–1 |
| South China | 3–5 | Bangkok Bank | 3–2 | 0–3 |
Semifinals
| Shimizu S-Pulse | 0–0 (a.e.t.) | Bangkok Bank |
|---|---|---|
| Penalties | ||
| 4–2 | ||
| Al-Zawraa | 2–1 | Navbahor Namangan |
|---|---|---|
| Ahmed Sabie 45' Mohammed 102' |
Sherzod Nazarov 36' |
Third place match
| Bangkok Bank | 3–1 | Navbahor Namangan |
|---|---|---|
| Apichart Thaweechalermdit 4' (pen.) Apiruck Sriaroon 36' Nawee Hatihakreangkrai 38' |