Hill led the NBHL in goals during the 1936-37 with 18 in 15 games. That same year, his team competed for the Allan Cup, and Hill tallied 22 points in 14 games. Signed as a free agent by the Boston Bruins in 1937, he spent most of the season with Providence Reds of the IAHL.
He did make his NHL debut that year, however, appearing in six games for Boston. The following year he was a full time Bruins forward, playing in 46 regular season and 12 playoff games to help the Bruins to the Stanley Cup championship. Hill earned his nickname this playoffs by scoring a record three successive overtime goals. The following year, he again played exclusively in Boston, putting up 20 points in 38 games. At the end of the 1940-41 season with the Bruins, Hill was again hoisting the Stanley Cup.
That truned out to be his finale in Brooklyn, as he was traded to the Brooklyn Americans for cash in June. In 47 games with Brooklyn , Hill tallied 37 points. His rights were transferred to Toronto during the special dispersal draft in October 1942, and suited up for 49 games with the Leafs, contributing 44 points. A broken ankle 17 games into the 1943-44 season sidelined Hill until the following fall, when he came back to help the Leafs to the 1945 Stanley Cup championship.
He played 35 games for Toronto the following year, and was then sent to the Pittsburgh Hornets of the AHL. He played the next two seasons for the Hornets, and the following four for the Regina Caps before retiring from play in 1952.