Robert 'Bob' McCaskill (27 September 1895 – 27 June 1952) was an Australian rules footballer who played for Richmond in the Victorian Football League (VFL) during the 1920s and coached both North Melbourne and Hawthorn.
McCaskill was a centreman while at Richmond and played finals football in 1924 with his side eventually finishing second in that year's unique round robin format.
After leaving Richmond he turned to coaching and had success as coach of Bendigo Football League club Sandhurst, leading them to six premierships in a row. For most of the 1940s he was the coach of North Melbourne and in 1947 became the first to coach 100 games for the club. They finished the 1945 home and away season in third but lost to Carlton in the first Semi Final thus being eliminated. He finished his coaching career with a stint at Hawthorn, going winless in the first year but winning four in the second. He was replaced by Jack Hale as acting coach in 1952 because of illness. He died in June 1952.