| Tourney Name: | Arab Cup Winners' Cup |
| Year: | 1999 |
| Other Titles: | الكأس العربية للأندية الفائزة بالكؤوس 1999 |
| Country: | Kuwait |
| City: | Kuwait City |
| Dates: | 1 – 20 November 1999 |
| Num Teams: | 7 |
| Confederations: | UAFA |
| Venues: | 2 |
| Cities: | 1 |
| Champion Other: |  Al-Ittihad |
| Count: | 1 |
| Second Other: |  Al-Jaish |
| Third Other: |  Al-Faisaly |
| Fourth Other: |  Al-Masry |
| Matches: | 12 |
| Goals: | 30 |
| Top Scorer: |  Frank Seator (7 goals) |
| Player: | Maher Al-Sayed |
| Goalkeeper: | Amer Al-Kaabi[1] |
| Fair Play: | Al-Faisaly |
| Prevseason: | 1998 |
| Nextseason: | 2000 |
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.[2]
Qadsia SC (the hosts) and MC Oran (the holders) qualified automatically.
Qualifying tournament held in Port Said, Egypt.
|-!colspan=3|Day 1 |-!colspan=3|Day 2 |-!colspan=3|Day 3 Al-Masry & Al-Riyadh SC advanced to the final tournament.
ASC Air Mauritanie advanced to the final tournament.
Qualifying tournament held in Amman, Jordan.
|-!colspan=3|Day 1 |-!colspan=3|Day 2 |-!colspan=3|Day 3 Al-Faisaly & Al-Jaish advanced to the final tournament.
ASC Air Mauritanie disqualified after arriving late.
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