Rolland W. Friedley (1937-39), a Carrothers, Ohio native, was one of the first standout men's basketball players for Tiffin University in the pre-World War II era. He enjoyed a banner season in 1937-38, leading the Dragons to a then-record 12 wins while earning Most Valuable Player honors. He led the region in scoring with 176 points and was on his way to another impressive season when an injury ended his career. Tiffin University's success during this period paved the way for the move to intercollegiate play. He earned a degree in Accounting and started Friedley Insurance in New Washington, Ohio in 1953. He served as President of the Farmers State Bank from 1968-92, where he was also Chairman from 1992-96. He served on Tiffin University's Board of Trustees from 1963-96. He died on July 24, 1996.

Tom Coffman, a Greenville, Ohio native, served as Athletic Director for Tiffin University for five years (1974-78, 1980-81). During that period, he helped the Dragons grow into a nationally recognized athletic institution. He was instrumental in leading Tiffin University into the National Association of Intercollegiate Athletics (NAIA) in 1974. During his first tenure as Athletic Director, the university witnessed the overall expansion of its athletic programs. In 1981 he served as Tiffin University's first Director of Development. He is a 1974 Heidelberg College graduate with a Masters in Education from Bowling Green State University. He currently serves as President and CEO of the Orthopedic Research and Education Foundation located in Rosemont, Illinois. He, his wife Deborah, and two children reside in Arlington Heights, Illinois.

Greg Freeman (1985-87) played football for Tiffin University in its first two seasons. Freeman amassed passing records that remain unbroken, including career completions (305) and yards (4075). The two-time All-District 22 selection also set records for season yards (2210) and most yards in a game (475). After his Tiffin University career, Freeman went on to place 12th of 25 quarterbacks at the National Football League Combine in 1988. He played professionally from 1991-94 in the Arena Football League. After his professional career, he founded American Glass in Denver, Colorado. He, his wife Rhonda, and two children reside in Elizabeth, Colorado.

Keith Ludrowsky (1983-87) was Tiffin University's top run producer during the 1980s. The Portage, Ohio native was an All-District and two-time All-Mid-Ohio Conference athlete before his career was ended due to injury. He still holds the school record for doubles in a career (41) and ranks in the top five of four offensive categories. He graduated with a degree in Business Management and currently works for the United States Postal Service. He, his wife Tina, and two children reside in Willowick, Ohio.

Phil Walford (1984-87), an Aldridge, England native, helped lead Tiffin University to four consecutive Mid-Ohio Conference Championships from 1984-87. He was a multiple All-Mideast Region and All-District 22 performer and a four-time All-Mid-Ohio Conference honoree. During his tenure with the Dragons, the men's soccer team achieved national recognition for the first time, cracking the NAIA Top 20. He earned his degree in Hotel/Restaurant Management and works at the Port  Columbus International Airport. He resides in Columbus, Ohio.