Maxwell remained in the game, turning to coaching. He served two seasons as coach of the Winnipeg Monarchs before moving to the cross-town rival Winnipeg Falcons. He led the Falcons to the 1920 Allan Cup, defeating the University of Toronto Varsity Blues by scores of 8–3 and 3–2. The victory also earned his team the right to represent Canada at the first Olympic ice hockey tournament at the Summer Games in Antwerp. His business interests outside of hockey prevented Maxwell from travelling to Belgium with his team; however the International Ice Hockey Federation (IIHF) lists him as the coach for the gold medal winning Canadians, who outscored their opponents 29–1 in three games played.