Success possibly could be an understatement when analyzing the coaching career of Bob Gillespie at Ripon College. In 28 years under his guidance, the men's basketball program has had just two losing seasons, while also having a string of 22 consecutive winning campaigns from 1983-2004. His teams have eclipsed the 15-win mark 21 times and the 20-win plateau in five different years, including twice in the past eight seasons. Ripon has won an average of 16 games a season during his career. The Red Hawks also experienced a school record 23 wins during the 1997-98 season, which included a 21-game winning streak.

Currently one of the top 15 Division III active coaches in the country in winning percentage (.689), Gillespie is also Ripon's all-time winningest coach (457-206). As head coach of the Red Hawks, Gillespie has led his teams to conference championships in 1986, 1987, 1991, 1992, 1998 and 1999. He also has led his squad to the NCAA Tournament on 10 occasions, most recently in 2002.

Gillespie has coached some of the best and brightest players in the league, three of whom were named All-Americans and one who was named an Academic All-American. He has coached five players to All-Region honors and 39 to the All-Conference first team. Gillespie was honored for his brilliance during the 1997-98 season as he was named Midwest Conference Coach of the Year.

A 1971 graduate of Lewis University, Gillespie began his coaching career at Wausau Newman High School before joining Ripon during the 1979-80 season as an assistant under long-time legend K.G. "Doc" Weiske, Ripon College class of 1950. Gillespie received his master's degree from UW-Oshkosh in 1982.

Gillespie also serves as an associate professor of physical education, head baseball coach and athletics director. He and his wife, Penny currently reside in Ripon.