The 2008–09 season finished with the Couchiching Terriers taking the overall best record. The finish in the Central Division was quite unique. First and last place in the division was the least spread out of all four divisions, the top six of eight teams all had even or winning records, the Markham Waxers and Wellington Dukes race for first place lasted until the final game of the season, as did the race for third between the Hamilton Red Wings, Newmarket Hurricanes, and Toronto Jr. Canadiens. The Central Division playoffs was won by Wellington, but they were eliminated by the MacKinnon Division champion and defending league champion Oakville Blades in a controversial series that went to a seventh game. The Kingston Voyageurs won the Ruddock Division who beat the Phillips Division champion Huntsville Otters 4-games-to-1 to go to the Buckland Cup finals. Kingston would defeat Oakville 4-games-to-2 in the league final for the Buckland Cup. The Voyageurs moved on to the Dudley Hewitt Cup in Schreiber, Ontario where they started the tournament by beating the host Schreiber Diesels of the SIJHL 9–0. They then were upset by the SIJHL champion Fort William North Stars 1–0. In the third game, the Voyageurs defeated the NOJHL champion Soo Thunderbirds 2–0 to move on directly to the DHC Final. In the final, the Voyageurs defeated a fatigued and fresh off a slim semi-final victory North Stars 4–1 to win the Central Canada crown. They then flew out to Victoria, British Columbia for the 2009 Royal Bank Cup. The event was a learning experience for the Voyageurs who started off the event with a 5–0 loss to the host Victoria Grizzlies. In their next game, the Voyageurs edged the MJAHL's Summerside Western Capitals with a wild 7–5 win. They then lost to the SJHL's Humboldt Broncos 5–2 and then the BCHL's Vernon Vipers 8–5. Edging into the semi-finals via a head-to-head win over the Capitals, the Voyageurs lost their final game of the year 6–3 to the eventual national champion Vipers.