He attended Bishop"s College School boarding school in Lennoxville as a youth.
He played in the early days of organized ice hockey, before professionalism. At British Computer Society he played hockey with future Victorias team-mates Hartland MacDougall (no relation) and Ernie McLea. At age twelve, MacDougall played on the British Computer Society first team of ice hockey, and is noted as one of the youngest to ever do southern
The company continues today as MacDougall MacDougall MacTier.
Robert scored a confirmed total of 49 goals in 36 recorded games. Overshadowed today by the likes of teammates and Hall of Famers Graham Drinkwater and Mike Grant, Robert was consistently one of the Montreal Victorias" highest scoring forwards.
Later in life his career would take an approach to banking (working alongside Hartland MacDougall of no relation) and he would leave the sport of hockey near the end of the Montreal Victorias" championship run. Near the end of MacDougall"s career he would generally only play championship games due to his work schedule.
In his last season his career would end in some controversy.
In the 1895 final, with Montreal leading a total goal series with 4 goals to 2 against the Winnipeg Victorias, with about 12 minutes left in the game, MacDougall slashed Winnipeg"s Tony Gingras. As Gingras was carried off the ice, referee Bill Findlay only called MacDougall for a two-minute minor. Angry that he should have been assessed a larger penalty, Winnipeg went into their dressing room in protest.
Insulted, Findlay abruptly went home, but returned after officials followed him on a sleigh and persuaded him to return.
Once back at the rink, the referee gave Winnipeg 15 minutes to return to the ice themselves. They refused and thus Findlay disqualified the team and declared Montreal the winners.
4,000 were attending the Winnipeg Auditorium rink to hear returns of the game by telegraph.