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.
Cross graduated from Harvard Law School in 1900 and settled in Providence, Rhode Island, where he established a law firm and worked as an assistant attorney general for the state of Rhode Island. He died in 1955.