Anderson attended Commercial High School in Brooklyn, New York, where he gained recognition as one of the top tennis players to hail from the city.

[7] Anderson won the Brooklyn championships in 1920 beating Frank Hunter in the final after coming from 5-2 down in the fifth set to win five straight games.

[2][3] He also won the singles title beating Robert Baird of Toronto, in a match in which "the superior speed of the younger man" proved decisive.

[2] At the 1923 US Championships, Anderson overcame veteran former finalist Nat Niles in the opening round in a long five set match.

"Anderson was putting all he had into his service and volleying, yet it seemed at times that the skill born of long experience that was the Londwood veteran's would triumph.