With only two of their remaining pieces from the "Why Not Us?" team still intact, Brian Connelly and Jimmie Covington, the Danes would look to rebuild with eight newcomers to the team. They would start the season 0–2 after matchups with Big East opponents Villanova and DePaul in "homecoming" games for their seniors. A 5–0 run after the slow start would put the Danes' in prime position to upset their crosstown rival Siena Saints, who had just endured 3 loses over 4 days at the 2008 Old Spice Classic in Orlando, Florida. However the Danes' would fall short by seven points. The Great Danes would win three of their next four games including a game postponed for snow and difficult travel conditions in Fairfield, Connecticut, against Sacred Heart before closing out the calendar year against the defending national champions Kansas Jayhawks. The purple-and-gold squad would fall behind early and not show any signs of life against the Jayhawks, in a 79–43 loss on nationally televised ESPNU.