1999 Arab Cup Winners' Cup

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.

!colspan=3|Day 1 (8 August)

!colspan=3|Day 2 (10 August)

!colspan=3|Day 3 (13 August)

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.

!colspan=3|Day 1 (10 September)

!colspan=3|Day 2 (12 September)

!colspan=3|Day 3 (14 September)

Al-Faisaly & Al-Jaish advanced to the final tournament.

Group A
ASC Air Mauritanie disqualified after arriving late.