Philippou was born in Limassol on 29 November 1979.
Philippou began boxing in 1994 and had his first fight six months later. In 2005, his best friend and coach Polis encouraged him to move to the United States to become a professional. Costas fought in the Golden Gloves two months after coming to the United States, but lost in the finals at Madison Square Garden by a split decision to Nagy Aguilera. Philippou then turned pro and had three fights three wins, the third being featured on ESPN. Costas transitioned to MMA after disputes with his manager and coach.
Philippou made his professional MMA debut in May 2008 for the Ring of Combat promotion, losing to fellow future UFC fighter Ricardo Romero by split decision. However, he subsequently amassed a record of 7 wins, 1 loss and 1 no contest within that promotion. Philippou had previously trained with the Serra-Longo Fight Team, but as of May 30, 2013 he decided to switch camps to Bellmore Kickboxing Academy. According to Matt Serra, Philippou left the team on good terms.

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