The 1999–2000 Iraq FA Cup was the 23rd edition of the Iraq FA Cup as a club competition. The tournament was won by Al-Zawraa for the third time in a row and the 14th time in their history, beating Al-Quwa Al-Jawiya 4–3 on penalties in the final after a 0–0 draw. Al-Zawraa also won the League, the Umm al-Ma'arik Championship and the Super Cup in the 1999–2000 season to become the second Iraqi side to win the domestic quadruple.
Al-Karkh won 4–3 on aggregate.
Samarra won 3–2 on aggregate.
Salahaddin won 9–1 on aggregate.
Al-Difaa Al-Jawi won 5–3 on aggregate.
Al-Shabab won 1–0 on aggregate.
3–3 on aggregate. Al-Jaish won on away goals.
Al-Bahri won 6–2 on aggregate.
Al-Quwa Al-Jawiya won 7–1 on aggregate.
1–1 on aggregate. Haifa won on away goals.
Al-Minaa won 2–0 on aggregate.
Erbil won 4–0 on aggregate.
Al-Najaf won 2–1 on aggregate.
Balad won 3–2 on aggregate.
Diyala won 7–3 on aggregate.
1–1 on aggregate. Al-Ramadi won 4–2 on penalties.
Al-Zawraa won 4–0 on aggregate.
Al-Karkh won 6–1 on aggregate.
Al-Difaa Al-Jawi won 2–1 on aggregate.
Al-Jaish won 2–1 on aggregate.
Al-Quwa Al-Jawiya won 4–1 on aggregate.
Al-Minaa won 2–1 on aggregate.
Erbil won 2–1 on aggregate.
Diyala won 5–0 on aggregate.
Al-Zawraa won 12–0 on aggregate.
Al-Karkh won 4–0 on aggregate.
Al-Quwa Al-Jawiya won 5–4 on aggregate.
Al-Minaa won 2–1 on aggregate.
Al-Zawraa won 5–0 on aggregate.
Al-Quwa Al-Jawiya won 2–0 on aggregate.
Al-Zawraa won 3–0 on aggregate.
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