Cross played center for Yale University's football team from 1893 to 1895. He was also an accomplished track and field athlete, competing in the hammer throw. In 1896, he was ranked as the second-best hammer thrower behind James Mitchell. In 1896, Cross became the head football coach at Stanford, guiding the team to a 2–1–1 record and a Big Game victory over Cal. He coached the team again in 1898, earning a 5–3–1 record.