Diana Drury began her coaching career at St. Lawrence College (Kingston) in 1985, and coached 15 teams in four different sports over the course of next eight seasons.

During this period, Drury's teams won provincial championships in three consecutive years, beginning with Division II women's basketball in 1985-86 and 1986-87, then women's soccer in 1987-88.

She is a three-time OCAA coach of the year winner, including once in basketball (1990) and twice in soccer (1991 and 1992).

In November of 1992, Drury received her most prestigious award, the CCAA Canadian Coaching Excellence/Coach of the Year Award for women's soccer. She is particularly proud of having coached fellow OCAA Hall of Fame member Denise Morey. Under Drury's tutelage, Morey led women's basketball in scoring (1988-89), and was selected as an all-Canadian in women's soccer (1991).

In 1999, Drury was an inaugural inductee into the St. Lawrence College Athletics Wall of Fame, and St. Lawrence College (Kingston) has named the Diana Drury Scholarship Bursary, after her.

Drury was Athletic Director at St. Lawrence in 1988 and then from 1994 to 2002, and has also contributed as a serving member of the CCAA, taking on the roles of women's soccer convenor and vice president of programs.