The 1999 Arab Cup Winners' Cup was the 10th edition of the Arab Cup Winners' Cup held in Kuwait City, Kuwait between 1 – 20 November 1999. The teams represented Arab nations from Africa and Asia. Al-Ittihad from Qatar won the final against Al-Jaish from Syria for the first time.
Qualifying round
Qadsia SC (the hosts) and MC Oran (the holders) qualified automatically.
Zone 1 (Gulf Area) Semifinals
Final
Al-Ittihad advanced to the final tournament.
Zone 2 (Red Sea) Qualifying tournament held in Port Said, Egypt.
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Al-Masry & Al-Riyadh SC advanced to the final tournament.
Zone 3 (North Africa)
ASC Air Mauritanie advanced to the final tournament.
Zone 4 (East Region) Qualifying tournament held in Amman, Jordan.
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Al-Faisaly & Al-Jaish advanced to the final tournament.
Group stage
Group A
ASC Air Mauritanie disqualified after arriving late.