The Prophet ﷺ performed Umra four times. The first was the Umra of Hudaybiya, the second was the Umra of Compensation in Dhul Qadah of the following year, the third was the Umra from Jirana, and the fourth was the one combined with his Hajj.
حدثنا يونس حدثنا داود بن عبد الرحمن عن عمرو بن دينار عن عكرمة
اعتمر النبي ﷺ أربعا عمرة من الحديبية وعمرة القضاء في ذي القعدة من قابل وعمرة الثالثة من الجعرانة والرابعة التي مع حجته
Its isnad is sahih. Dawud bin Abdul-Rahman is al-Attar, and he is trustworthy, as we said at 1710, and Bukhari gave him a biographical entry in al-Kabir 2/1/220. The hadith was narrated by Tirmidhi 2:80, who said, "A gharib hadith." Ibn Uyayna narrated this hadith from Amr bin Dinar from Ikrima, that the Prophet ﷺ performed umrah four times, without mentioning in it "from Ibn Abbas," then he narrated it as such by way of Ibn Uyayna. It seems he wants to fault this connected chain by means of the disconnected one, but this is not a real defect.Its commentator said, "It was also transmitted by Abu Dawud and Ibn Majah, and Abu Dawud and Munziri passed over it in silence, and all its narrators are trustworthy."Jirana, with a kasra on the jim and the ayn and a doubled ra, though some say the ayn takes a sakin, is a place located six or nine miles from Makkah.