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Cassar played college soccer at Florida International University, where he was roommates with Steve Ralston. Following his graduation, he was selected 8th overall in the 1996 MLS College Draft by the Dallas Burn. Although Cassar made the team, Mark Dodd took firm hold of the starting position, and Cassar only appeared in two games that season. After spending all of the 1997 season injured with a torn ACL, Cassar was selected 10th overall in the 1997 MLS Expansion DraftThe 1997 MLS Expansion Draft was held November 6, 1997. Two teams participated, the Chicago Fire and Miami Fusion F. both expansion clubs planned for the 1998 season. Each team selected 12 players from a pool of players that each present Major League Socc by the Miami FusionThe Miami Fusion played in the Major League Soccer (MLS) from 1998 to 2001. The Miami Fusion played in Lockhart Stadium in Fort Lauderdale, Florida, which was a former high school stadium converted into a soccer-specific stadium. The MLS contracted follow. Cassar started much of the Fusion's inaugural season, appearing in 21 games, all starts, and compiling a GAA of 1.95. After splitting starting duties with Garth Lagerway in 1999, Cassar lost his job to Nick RimandoNick Rimando (born June 17, 1979 in Montclair, California) is an American soccer goalkeeper, who currently plays for D. United of Major League Soccer. Rimando played two years of college soccer at UCLA. As a rookie in 1997, he tended goal as the Bruins wo, and would start just ten games for Miami in 2000 and 2001. Upon Miami's contraction at the end of the 2001 season, Cassar was again selected by the Burn in the 2002 MLS Dispersal DraftThe 2002 MLS Dispersal Draft was held by Major League Soccer, following the contraction of the Miami Fusion and Tampa Bay Mutiny to distribute the two teams' players that were not selected in the 2002 MLS Allocation Draft. Round 1 Round 2 Round 3 MLS Draf, but failing to make the team, went looking for work overseas. Cassar found a job as the backup for the Bolton Wanderers in England, and would remain with the team from March to June of 2002.
Cassar returned to the United States at the end of the English season, and signed with the Atlanta SilverbacksThe Atlanta Silverbacks are an American professional soccer club who currently play in the A-League, a division of the United Soccer Leagues, and the second division in the US Soccer hierarchy. They currently play in DeKalb Memorial Stadium, in Atlanta, G of the A-League, for whom he appeared in six games. Cassar joined Dallas for a third time the next year, signing on as a backup for D.J. CountessDelvin "D. Countess (born January 9, 1982, in Bakersfield, California) is a soccer goalkeeper, who currently plays for Real Salt Lake in Major League Soccer. Countess was the starting goalkeeper for the United States team at the 1999 Under-17 World Champi following Matt Jordan's departure for Europe. Cassar appeared in seven games for the Burn in 2003, doing a passable, if unexceptional, job for the team. Following the 2003 season, the Burn brought in a new coach, Colin Clarke, who traded away Countess and replaced him with Scott Garlick . Although Garlick began the season as the team's starting goalkeeper, an injury midseason gave Cassar the opportunity to sieze the position, which he did with a series of impressive performances; he ended the season as the club's starting goalkeeper, having made 19 starts.