Leonidas Vokolos started his career playing for Panionios. Afterwards, he was transferred to Greek giants Panathinaikos, where he won the Double in 2004. He then played for PAOK FC, Kallithea F.C. in Greece and APOP Kinyras Peyias in Cyprus. Vokolos was known for his reliability in defence and his very good heading and jumping ability. He played as well for the Greece national football team.