The Messenger of Allah ﷺ performed four Umras, all of them in the month of Dhul-Qadah except the one that accompanied his Hajj. The first Umra was from Hudaybiyah, or at the time of Hudaybiyah, in Dhul-Qadah. The second was the following year in Dhul-Qadah. The third was from Jiranah, where he distributed the spoils of Hunayn, in Dhul-Qadah. The fourth was the Umra performed together with his Hajj.
أن رسول الله ﷺ اعتمر أربع عمر، كلهن في ذي القعدة إلا التي مع حجته: عمرة من الحديبية أو زمن الحديبية- في ذي القعدة، وعمرة من العام المقبل في ذي القعدة، وعمرة من جعرانة حيث قسم غنائم حنين في ذي القعدة، وعمرة مع حجته.
Bukhari narrated it in the Book of Umrah (1778), and Muslim (1253), both via Hammam, who said, Qatada narrated to us, that Anas told him, and he related it. The wording given here is Muslim's.