Wallingford came to Holy Cross and promptly became the starting quarterback of the football team as a freshman. He led his team to an amazing 3-0 upset of undefeated and nationally ranked Syracuse as a senior in 1920. He played with Hop Riopel, Ken Simendinger, Denny Gildea and Harold Gagnon, all Hall of Famers. After graduation, he received his medical degree from Albany Medical College. He also received an Honorary Degree from Holy Cross.