Reg Bentley, the least-known of the famous Bentley brothers, was born on May 3, 1914 in Delisle, Saskatchewan. Reg, though the oldest, arrived to in the National Hockey League later then his two brothers, who were already stars by the time he suited up. His path to the NHL and the Chicago Black Hawks was similar, though. Like his brothers, Bentley played Senior hockey with the Saskatoon Quakers, the Moose Jaw Millers, and the Drumheller Miners, and then spent a season with the Kansas City Americans before he finally ended up in the NHL.
In 1942-43, Reg Bentley joined his brothers Max and Doug with the Chicago Black Hawks. Though he played just eleven games and scored only one goal and two assists, he did make history. New Year's Day, 1943, marked the first time three brothers were sent out as linemates in an NHL game. Two days later, on January 3, 1943, Reg Bentley scored his only NHL goal. The assists went to brothers Doug and Max, making it the only time in NHL history a goal has been scored with all of the scoring points assigned to the same family.
Though Reg Bentley didn't enjoy the NHL success that his younger brothers did, he was able to have a long professional career at other levels. After his NHL tour of duty, Bentley played nine more seasons of professional hockey, with stops in five different leagues. His most successful season in terms of personal numbers came in 1946-47 with the New Westminster Royals of the Pacific Coast Hockey League. That year, Bentley scored 41 goals and 71 points in sixty games.
Reg Bentley retired following the 1951-52 season