On November 17, 2007, McCaffery guided Siena to a 79–67 victory over #20 ranked Stanford at the Times Union Center in Albany. The win was Siena's first over a ranked opponent since their first-round victory against the Cardinal in the 1989 NCAA tournament. Siena finished the regular season at 19–10 and 13–5. They tied with Rider for first place in the MAAC. The Saints defeated Manhattan, Loyola and Rider on their way to winning the MAAC championship and an automatic NCAA tournament bid. It was the Siena's fourth trip to the NCAA Tournament and their first under the guidance of McCaffery. In March 2008, the 13th seeded Saints soundly defeated #4 Vanderbilt 83–62 in the first round of the NCAA Tournament in the Midwest Region. Siena's season ended one game short of the sweet sixteen in an 84–72 loss to 12th seeded Villanova. Siena finished the season at 23–11. It was the most wins for a Siena team since the 1999–2000 season.