Lori Stich Obluda
Posted September 28, 2026
Winningest basketball coach
For 33 years, Bob Gillespie took Ripon College athletics to new heights as a basketball coach, baseball coach, athletic director and associate professor of physical education. He remains today as the winningest basketball and baseball coach in Ripon College history with a combined record of 869-536-3.
Robert G. Gillespie was born March 27, 1949, in Chicago, Illinois. He earned his undergraduate degree from Lewis University in 1971 and his master’s degree from the University of Wisconsin-Oshkosh in 1982. Gillespie began his coaching career at New Holland High School in Illinois, then spent four years at Wausau Newman High School before joining Ripon during the 1979-80 season.
He served that year in basketball as an assistant under longtime legend Kermit “Doc” Weiske, Class of 1950, and assumed the head baseball coaching duties. His 32-year head basketball coaching career began the following year with the 1980-81 season. During that time, his teams were 510-248. Gillespie was one of the top 15 Division III active coaches in the country and his winning percentage of .673 ranks him among the top 40 in Division III history.
The basketball teams under Gillespie’s leadership were led to six Midwest Conference championships and four wins in 10 NCAA Division III tournament appearances. A high point was the 1997-98 campaign in which Ripon won a school record 23 games including 21 consecutive victories and a perfect 16-0 conference mark. Gillespie was Midwest Conference Coach of the Year that year. He was inducted into the Ripon College Athletic Hall of Fame in 1996 and the Wisconsin Basketball Coaches Association (WBCA) Hall of Fame in 2008.
Gillespie served as the head baseball coach for 23 years from 1980-1995 and 2006-2012. On the baseball diamond, Gillespie led Ripon to seven Midwest Conference championships and five NCAA Division III baseball tournament appearances while accumulating a 342-269-3 (.559) record. In 2006, his team was the first Midwest Conference team to ever go 16-0 during the regular season. The 2006 team won two NCAA regional victories, losing only in the regional final game, one shy of a World Series berth.
Gillespie’s father, National Baseball Coach Hall of Famer Gordie Gillespie, led the Red Hawks as head baseball coach from 1996-2005. During his father’s 10-year father’s tenure, Gillespie served as the associate head coach. He was a crucial component in six additional Midwest Conference championships as an assistant under his father.

Bob Gillespie, right, with his wife, Penny, and son, Scott GIllespie, Class of 2011.
Ripon honored Gillespie with the May Bumby Severy, Class of 1908, Award.for excellence in teaching, and in February 2010, the basketball court at Weiske Gymnasium was named Bob Gillespie Court in his honor. He retired from Ripon in May 2012.
“I know I will never be able to accurately describe my feelings for Ripon College and the many great players I have had the privilege to coach,” Gillespie said. “The experience and memories my family and I have from my time at Ripon College have been wonderful. I was able to coach baseball with my father for 10 years, and coaching my son, Scott, Class of 2011, in basketball was the biggest thrill I’ve ever had as a coach.”