"In the fall of 1961 a group of Weyburn businessmen realized the fruition of their dreams as the first Weyburn Red Wing hockey team skated onto the Colosseum ice. The committment and efforts of these men initiated a junior hockey movement that has become the most successful sports franchise in our city's history, and this phenomenon has started hockey fans in this area on the most exciting and thrilling roller-coaster ride their entertainment dollar could ever purchase."
- Trevor Bell (from "Sharing the Glory")
The Weyburn Red Wings were one of the founding members of the Western Hockey League in 1966, but left in 1968 to return to the SJHL. Increasing travel costs of playing in the Western Hockey League was the main reason for moving back to the SJHL.
The team is the most successful in the league in terms of league championships won. They have won 8 SJHL championships in their history. They won it in 1970, 1971, 1984, 1994, 1995, 1997, 1998, and 2001.
The Red Wings won the Royal Bank Cup, representative of national Canadian Junior A Hockey League supremacy, in 2005. They won the Cup on home ice, defeating the Camrose Kodiaks 3–2 in front of 2,152 fans in the championship game. They also won the trophy in 1984, defeating the Orillia Travelways 3–0 in the seventh game in front of 2,375 fans at the Weyburn Colosseum.