In 1942, and from 1946 to 1948, he played college football for Murray State, and was left guard for their 1948 conference championship team.

[2] He missed seasons between 1943 and 1945 due to serving in the United States Army in World War II.

[3] After graduating college with a bachelor's and master's degree, Cullivan started a coaching career, being named assistant at Fulton High School in Kentucky in 1949.

[8][9] After leaving Murray State, Cullivan took a year off from coaching to work on a doctorate from University of Indiana.

[12] After two seasons with Appalachian State, he was signed by Grove High School in 1966 as defensive coordinator and head coach.

[15] After a stint with them, he had a short stay with a team in the United Professional Football League (UPFL) before retiring.