In 2005, the Siena Saints were picked to finish last in preseason polls for the Metro Atlantic Athletic Conference. However, McCaffery orchestrated the fifth greatest turnaround in all of Division 1 and guided Siena to a 15–13 record. The team earned several memorable victories in the regular season, including an 82–74 win against cross-town rival Albany, and an 82–76 triumph at eventual MAAC champion Iona. The Saints clinched a first-round bye in the MAAC tournament with a 98–92 double-overtime victory over Niagara on the team's senior day. Siena's season ended with a 63–62 loss to St. Peter's in the MAAC quarterfinals.