In October 1215, Oliver's father rewarded him with a cask of wine.[5] In November 1215, he was given the castle of Tonge. The regents of his half-brother, Henry III, confirmed this grant in June 1217.[2][5] In July 1216, he was granted the manor of Erdington. In March 1218, he granted control of the estate of Hamedon until Eve de Tracy could reclaim by payment of sixty marks.[5] Eve was probably Oliver's mother's sister.[2]
Oliver joined the Fifth Crusade in 1218.[2] In doing so, he may have been discharging his late father's unfulfilled vow.[6] He raised 100 marks for his venture by pawning a royal wardship.[7] With a group of English crusaders, he landed at the siege of Damietta in September or August. He died at Damietta in late 1218 or early 1219.[2] It is unclear if he died of an illness or in battle.[5] His body was returned to England and buried in Westminster Abbey. There is no record that he married.[2]