Will Anderson was born and raised in Toronto, the son of Alexander Anderson, a wealthy merchant who owned an estate at Jacksons Point on Lake Simcoe. He was a competitor in local cycling events in Toronto from the young age of 13, and was a student at Harbord Collegiate Institute in Toronto when he was chosen to compete at the Olympics in 1908. He won a bronze medal in the 1,980 yards team pursuit alongside Walt Andrews, Fred McCarthy, and William Morton. Anderson also entered the 5,000 metres, the 20 kilometers, and the 100 kilometers, but did not advance beyond the opening round of any of those events. Following the Olympics, Anderson later joined the Toronto Bicycle Club and competed in many local cycling races, alongside the likes of his fellow Olympic competitors, including at the Canadian Cycling Championships in 1908. He was a fierce competitor who formed legendary rivalries with his peers in local events, in particular from 1908 to 1909 with his former Olympic teammate Walt Andrews of the Royal Canadian Bicycle Club (RCBC).
Anderson announced his retirement from bicycle racing in early 1910, but briefly returned later that year to face Andrews once again in August. He later took to motorcycle racing, forming another storied rivalry with fellow racer Herb Kipp, lasting until his retirement in 1911. Anderson married Harriet Grace Rankin in that same year and lived briefly in New Brunswick before moving back to Toronto, working as an automobile salesman. He died at the age of 40 of a brain tumor in 1928 at a hospital in Boston, where he went to seek treatment.