Siena was ranked highly in preseason publications entering the 2008–09 season. The Saints convincingly won their first two games against Boise State and Cornell.McCaffery guided Siena to victories in 25 of their final 30 games. Siena won games against St. Joe's, Northern Iowa, Albany and Buffalo along the way. Siena's 16 MAAC wins tied a league record for regular season wins. Siena would go on to win the MAAC championship (and clinch a second straight NCAA tournament bid) by defeating Canisius, Fairfield and Niagara. McCaffery led the Saints to the most single season wins in their Division I history and earned the 2009 MAAC coach of the year.