Born in Kalabaka, Vakouftsis began playing football for Panathinaikos' youth side.
His early performance was one of the key factors for Vakouftsis to gain the nickname "Il Greco Batistuta", due to the Argentine legend striker of Viola.
His return in the Greek Superleague for Iraklis FC on loan did not meet expectations, and in 2002 he moved in Cyprus to play for APOEL and later for rivals AC Omonia.
Vakouftsis played only three games for Xanthi in the league and because he was considered as a backup for the first team he requested a transfer.
His former clubs include: Panathinaikos, ACF Fiorentina, Ravenna Calcio, Iraklis FC, APOEL, AC Omonia, Ergotelis F.C.