[4] Day was a two-sport athlete at West Chester University, where he competed in football and track and field.
[5][6] In 2003, Day accepted an assistant coaching position on the women's basketball staff at Duquesne, and would have subsequent assistant coaching stops at La Salle, Saint Joseph's, Indiana, and Penn.
On May 11, 2016, Day was named 8th head women's basketball coach at Vermont, replacing Lori Gear McBride.
[7] On April 2, 2018, Vermont announced it was "reviewing certain aspects of the women’s basketball program" focused on Day's verbal interactions with players.
[3] Upon taking an assistant coaching position at La Salle on May 8, 2018, the Burlington Free Press reported that Day will receive $142,800 in severance pay, and the investigation into his conduct was "discontinued, and no report has been or will be issued."