Barbara started his career as a youth player with Qormi. After having been spotted by scouts following some impressive displays, he earned a move to play in the Maltese Premier League with Floriana in July 1999. Early in his career with them, he was often used in defensive positions and although he played 74 games with the club he only managed eight goals – all which were all scored during the 2001–02 season. In 2002, Barbara received his first call up to the Maltese national team due to a number of impressive performances for Floriana.