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.
| Tournament details | |
|---|---|
| Teams | 22 |
| Final positions | |
| Champions |  Shimizu S-Pulse (1st title) |
| Runners-up |  Al-Zawraa |
| Third place |  Bangkok Bank |
| Fourth place |  Navbahor Namangan |
First round edit
West Asia edit
| 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 edit
| 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 edit
West Asia edit
| 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 edit
| 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 edit
West Asia edit
| 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 edit
| 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 edit
| 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' |