Gerry was discovered by legendary Bruin scout "Baldy" Cotton. Cotton extended an invitation to the Bruin training camp for the 1959-60 season where he impressed the Bruin brass enough to offer him a spot on the Kingston Frontenacs of the Eastern Professional Hockey League. He tallied 35 goals and registered 42 assists in his rookie pro campaign.
He started the 60-61 season in Kingston, but the Bruins struggled miserably and were quickly looking for help. They gave Ouelette an opportunity to prove him when they recalled him to Boston.
Gerry played in 34 games, scoring 9 points including 5 goals. His most memorable goal had to be his first NHL goal, which he scored against the legendary Terry Sawchuk on November 3, 1960. Gerry's season was cut short by emergency appendectomy surgery in January of 1961. When he recovered from the surgery he was sent back to Kingston where he finished the season.
Gerry obviously didn't impress the Bruins braintrust enough during his 34 game stint. For the next 4 seasons he shuffled between Bruin farm teams in Providence, Minneapolis, Kingston and San Francisco. He played well, scoring more than 30 goals twice but never had another shot at the NHL.
In 1965, Chicago selected him in the reverse draft, and quickly assigned him to the Buffalo Bisons, where he was perhaps best known as a professional hockey player. He enjoyed a lot of success. He even served as team captain when the Bisons went to the AHL Calder Cup Championship in 1970. He is the 13th highest scorer in Bisons's AHL history
The Bisons folded in 1970 when the NHL Sabres began play. The following season Gerry joined the Omaha Knights of the CHL, where he captained that team to the Adams Cup. His 58 assists with Omaha in the 70-71 season lead the league, as did his 5 goals and 13 assists in 11 games during the playoffs.
After the 1970-71 season Red returned to his native New Brunswick and played on the Hardy Cup winning Campbellton Tigers. He later coached the Tigers to two more Hardy Cup wins in 1977 and 1988. Gerry also worked for the New Brunswick Recreation Department in Campbellton until 1993, when he retired.