His senior year, Cillo made five starts, completing one game (23 total appearances).

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.

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 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.

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.

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.

[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.