A quick attacking forward, Massara started his career in the youth ranks of Torino, but never managed to break through the first team and was eventually sold to Serie C1 club Pavia. In 1991 he joined Pescara, playing three years under head coach Giovanni Galeone, being featured as a wing forward in an attacking 4–3–3 lineup that successfully won promotion to Serie A in 1992. He made his Serie A debut in the 1992–93 season, in what would remain his lone top flight season as a player.