As anyone involved with amateur sport knows, it takes really dedicated volunteers to allow an organization or team to flourish. Roy Woolsey was just such an individual, lending a hand behind the scenes and on the floor at various levels of lacrosse in Victoria from the box game's beginnings in the mid-1930s through the 1970s. A Bobby-helmet wearing beat cop at first and later a desk sergeant with the Victoria police, Woolsey was well-known in the community and developed numerous contacts whom he could hit up to sponsor his teams. In the 1940s, having gained experience managing the Joker's junior and intermediate teams, he was well-equipped to help the club move into the Senior 'B' ranks. With his help, they won the B.C. championship in 1943 and in 1945. Roy used his managerial experience to get on the board of the Greater Victoria Lacrosse Association in the late 1950s and in 1970 became GVLA president. Along the way, he worked as a director with the Shamrocks, until joining the fledgling McDonald's Bakery sponsored Junior A program in the early 70s. With his instrumental help, they developed into a Minto Cup winner. While he was a gruff character on the outside, Roy Woolsey had a big heart, as folks who took in games at the Memorial Arena witnessed. He was often stationed at the arena entrance ensuring handicapped patrons had a decent place from which to watch the game.

Despite finishing last in their first season, the Cougars led the league in attendance figures. It was a different story in the 1950-51 season when they captivated Victoria hockey fans and culminated the season winning the Pacific Coast Hockey League and Play-off Championships. The Cougars won the league by a single point, Eddie Dorohoy had a 4-point night in the last game to claim the scoring title and playing-coach, Roger Leger, was named the league MVP. Their play-off semi-final went to seven games with four of the games decided in overtime. Victoria took the finals 4 games to 1.