Makdessi was born in Halifax, Nova Scotia, Canada on May 3, 1985, and is a first-generation Lebanese-Canadian born to Lebanese parents. His martial arts training started with Tae Kwon Do at the age of six. When Makdessi started high school, his dojo closed, and he could no longer continue. Towards the end of high school at the age of 19, he found a karate dojo where he learned Shotokan. Makdessi spent a lot of his time competing in kickboxing tournaments, and in 2006 won a gold medal in the USKBA. After going 22–0 in kickboxing, Makdessi began training in mixed martial arts.
Makdessi made his professional MMA debut in 2008 and compiled an undefeated record of 7-0 before being signed by the UFC.
Makdessi signed with the UFC in 2010. He made his promotional debut on December 11, 2010, at UFC 124 in Montreal, winning a dominant (30-27, 30–27, 30–26) decision over Pat Audinwood.

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