Dill played professionally in the American Hockey League alongside National Hockey League Hall of Famer Eddie Shore for the Springfield Indians, in the United States Hockey League for the Saint Paul Saints and in the National Hockey League for the New York Rangers. Throughout his hockey career, Bob Dill was considered an intense, but clean player with an aggressive style of play. While with the New York Rangers, Dill"s battles with Montreal Canadiens great Maurice "Rocket" Richard became the stuff of legend, and more recently, of Canada in the 2005 French Canadian film, The Rocket.
Dill was portrayed in the film by the then-active National Hockey League forward Sean Avery.
Bob Dill was also a star baseball player with the American Automobile Association Minneapolis Millers baseball team A minor league team of the New York Giants, the Millers organization was the "stopping point" for Ted Williams, Willie Mays and many other greats on their way to the "majors."
Dill was sought by the Giants Major League Baseball organization to play baseball in the major leagues.
Had Dill played for the Giants baseball team, he would have been the first (and only) American to play both National Hockey League hockey and Major League Baseball, and probably the first "two sport" player in American professional sports history. The proposed contract was nixed, however, by the New York Ranger hockey organization because the schedules of the two sports overlapped.
In that era, the National Hockey League contracts (and professional sports contracts in general) were more restrictive, and with players having far less latitude for making career decisions than they do today.
After the 1944-1945 National Hockey League season the New York Rangers sent Dill to the Rangers farm team, the Saint Paul Saints, because Dill was a Street Paul native and therefore he would be good for improving attendance, which he did. Dill went on to five more years of successful play for the Saints, He was a 1st team all star in 1947 and 1950 and led the Saints to a USHL Championship in 1948. Fans filled the stands to watch a great rivalry between the Saint Paul Saints and the Minneapolis Millers hockey team, one of whose star players was another Minnesota hockey legend, John Mariucci.
After serving as a player-coach for his old friend Shore in Springfield during the 1951-1952 season, Dill retired.
Following his playing days Dill worked as an National Hockey League scout for the New York Rangers, Chicago Blackhawks, and Minnesota North Stars.