Wiley quarterbacked the high-powered Crusader squads of the late 1980s which compiled a record of 43-9-1 during his four years, including a perfect 11-0 mark during the 1987 campaign. His teams won two Colonial League titles and three straight Lambert Cups, in addition to earning ECAC Team of the Year honors twice. At the time of his graduation, Wiley held Holy Cross records for most passing yards in a game (438 at Massachusetts in 1987), passing yards in a season (3,677 in 1987), passing yards in a career (9,698), touchdown passes in a game (seven at Lehigh in 1987), touchdown passes in a season (34 in 1987) and touchdown passes in a career (71).
He was selected as a first team All-American by the Associated Press, the Walter Camp Foundation and the American Football Coaches Association in 1987, in addition to receiving first team Academic All-America honors. A two-time first team All-New England and All-ECAC selection, Wiley was also chosen as the New England Offensive Player of the Year and the Patriot League Offensive Player of the Year in 1987.
After his senior season he earned an NCAA Post Graduate Scholarship and pursued a career in medicine.