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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.Tooltip Aggregate score Team 2 1st leg 2nd leg
Esteghlal Iran 15–0 Lebanon Homenmen 7–0 8–0
Al Arabi Kuwait (w/o)1 Iraq Al-Zawraa
Al Ittihad Yemen 1–4 Qatar Al Rayyan 0–2 1–2
Al Jaish Syria 2–2 (a) United Arab Emirates Al Ain 0–1 2–1
Kaisar Hurricane Kazakhstan 3–3 (4–3 p) Tajikistan Khujand 3–0 0–3
Al Ahli Saudi Arabia bye
Al Ittihad Saudi Arabia bye
Navbahor Namangan Uzbekistan bye

1 Al Arabi withdrew

East Asia

Team 1 Agg.Tooltip Aggregate score Team 2 1st leg 2nd leg
New Radiant Maldives 1–4 Vietnam Công An Thành Phố Hồ Chí Minh 1–3 0–1

Second round

West Asia

Team 1 Agg.Tooltip Aggregate score Team 2 1st leg 2nd leg
Al Ittihad Saudi Arabia 2–1 Iran Esteghlal 1–0 1–1
Al-Zawraa Iraq 5–4 Qatar Al Rayyan 5–2 0–2
Al Ahli Saudi Arabia 3–0 Syria Al-Jaish 1–0 2–0
Kaisar Hurricane Kazakhstan 2–3 Uzbekistan Navbahor Namangan 2–2 0–1

East Asia

Team 1 Agg.Tooltip Aggregate score Team 2 1st leg 2nd leg
Shanghai Shenhua China 0–2 Japan Shimizu S-Pulse 0–0 0–2
Sembawang Rangers Singapore (w/o)1 South Korea Anyang LG Cheetahs
Công An Thành Phố Hồ Chí Minh Vietnam 1–4 Hong Kong South China 1–1 0–3
Bangkok Bank Thailand 6–0 Indonesia Persebaya Surabaya 5–0 1–0

1 Sembawang Rangers withdrew before 1st leg

Quarterfinals

West Asia

Team 1 Agg.Tooltip Aggregate score Team 2 1st leg 2nd leg
Al Ittihad Saudi Arabia 1–2 Iraq Al-Zawraa 1–2 0–0
Al Ahli Saudi Arabia 6–31 Uzbekistan 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.Tooltip Aggregate score Team 2 1st leg 2nd leg
Shimizu S-Pulse Japan 5–2 South Korea Anyang LG Cheetahs 3–1 2–1
South China Hong Kong 3–5 Thailand Bangkok Bank 3–2 0–3

Semifinals

Third place match

Final

References

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