[1][2][3] Vendrame began his playing career in the Udinese youth sector at the age of 13, and later moved to Serie A side SPAL in 1967, but did not make a single appearance for the team.

He made his Serie A debut with Vicenza in 1971, where he rose to hero status due to his performances; he remained with the club until 1974, when he earned a move to Napoli; however, he only remained with the latter side for a season, as he soon fell out of favour with the club's strict manager – Luís Vinício – and struggled to gain playing time, obtaining only three appearances during his time with the team.

The first incident came in a 0–0 home draw against Cremonese during the 1976–77 season; in order to entertain the crowd during a rather dull and goalless match (the match had been fixed so that it would ultimately end in a 0–0 draw, as Cremonese only needed a single point to obtain promotion to Serie B,[4][7][8] with two games of the season remaining, while the result would not have affected Padova), he picked up the ball at the edge of the opposing penalty area and subsequently ran towards his half, dribbling through all the players of the opposing team as well his own team, including his own goalkeeper – after wrong–footing him with a fake shot – before finally stopping the ball on the goal–line and then starting the play back up again.

The second incident occurred when he stopped a home match at the Stadio Silvio Appiani in order to say hello to his friend singer–songwriter Piero Ciampi, whom he noticed was among the crowd watching the game in the stands.

He initially accepted, as Padova were facing financial difficulties at the time, and players only received match bonuses of 22,000 lire per point, the minimum amount allowed by the FIGC.

Possessing excellent technique, flair, dribbling skills, and an eye for the final pass, he was regarded as one of the most promising young Italian players early in his career,[5][6][8] even earning the nickname "the Italian George Best," due to his physical appearance (namely his beard and long hair),[4] skills, playing style, movements, position, rebellious personality, and anti–conformist "hippy" lifestyle off the pitch, which made him a symbol of Italian football during the 1970s, and highly popular with the fans, but also made his relationships with his managers difficult (indeed, Vendrame was known for both smoking and drinking throughout his career).