[4] His first competitive match came in the Old Etonians' 10–0 win at Brentwood in the first round of the 1880–81 FA Cup, playing as one of the two right-wingers, and making one of the goals by putting in a cross-shot turned in by Herbert Whitfeld.
He had more success in the 1881–82 FA Cup, playing in every round, and scored the only goal in the final against Blackburn Rovers, shooting just inside the post in the first ten minutes.
[10] By 1886, Anderson had moved to Montana as a cattle rancher, and in 1893 founded the Livingston, Independence and Cooke City Telephone Company.
After his brother Charles left him a large estate in 1893, he began to spend more time in Europe than the United States, finally emigrating back to Britain in 1896.
In 1899, he enlisted to fight in the Boer War, but resigned his commission as lieutenant in Thorneycroft's Mounted Infantry after only seven months,[11] and died on 23 June 1903, older brother Rupert being his heir and executor.