His senior year, Cillo made five starts, completing one game (23 total appearances). His record improved to 6–5 with four saves—giving Cillo a hand in ten of Birmingham's twelve wins. His 2.90 earned run average was 1.16 lower than the previous season, and .01 better than Brad Sullivan, a fellow Conference USA hurler who would go to the Oakland Athletics in the first round of the 2003 Major League Baseball draft. Cillo went unpicked in that draft and signed as a free agent with the Florida Marlins.
Cillo was released by the Marlins at the end of the 2004 season, and caught on with the Calgary Vipers of the Northern League for their inaugural season, 2005. Cillo's record was 4–2 with a 4.04 ERA and 3 saves for the Vipers, striking out 64 in 62.1 IP. He was traded to the Rockford RiverHawks for Frank James in January 2006, however, he never played for Rockford, making his way to Italy instead.
Italy
In his first season in Federazione Italiana Baseball Sotball in 2006,[3] Cillo was 7–4 with a 2.59 ERA for De Angelis Godo as the team (new to the A1 classification) missed the playoffs by one game. Cillo struck out 90 in 118.2 IP, finishing sixth in the league. He joined the Italian team for the World University Championship. In 2007, Cillo's record fell to 4–4, 3.31 for Godo. He was fifth in Serie A1 with 92.1 innings pitched. In the 2007 Baseball World Cup, Cillo fanned 7 in 6 innings for Italy, going 1–0 with a 1.50 ERA.
Cillo's one win came on November 9, as Italy beat Team USA 6–2. It was the U.S.'s first loss to Italy in 21 years and the first time it ever lost to Italy with professional players, as the team consisted of Major League Baseball players and top minor league prospects. Cillo relieved Luca Panerati in the top of the sixth with a 6–2 lead and pitched two innings of one-hit ball, striking out two, against a lineup that included Evan Longoria, Andy LaRoche, Delwyn Young, Justin Ruggiano, Steve Pearce, Colby Rasmus and Jayson Nix. Though he entered with a lead, Cillo got credit for the win because teenaged starter Matteo D'Angelo had not worked the required number of innings. It was the US's lone loss of the 2007 Baseball World Cup.
Cillo was a member of Fortitudo Baseball Bologna in 2008.[4]Bologna led the league in the win-loss column, with a pitching staff led by four hurlers with ERA below 2.00. Cillo had a 9–1 record in 14 starts, and his 1.34 ERA was second in the league to Telemarket Rimini's Gustavo Martinez (1.17). Cillo finished third in the Miglior Lanciatore Assoluto (Italian equivalent to the Cy Young Award) behind Martinez and T&A San Marino's Tiago DaSilva.[5]
2009 World Baseball Classic
Cillo once again joined team Italia for the 2009 World Baseball Classic. Prior to the start of the WBC, Italy played two Spring training games against the Washington Nationals and New York Mets. Cillo took the loss in the Nats' 9–6 victory over Italy, giving up a walk off home run to Roger Bernadina.[6] Against the Mets, Cillo pitched one inning, giving up one hit and striking out one in Italy's 3–2 loss.[7]
In the WBC, Cillo made two appearances in Italy's three games, giving up one earned run on a solo home run in one total inning pitched.[8] Following the WBC, Cillo chose not to resign with Bologna, deciding instead to rejoin the Calgary Vipers,[9] now of the Golden Baseball League.[10]
Pitching out of the bullpen in 2012, Cillo went 2–2 with a 1.19 ERA for the Fortitudo team that went on to win the European Cup.[15] He also won the European Championship with the Italian national team.[16]