The Wellesley Applejacks joined the Western Junior D Hockey League in 1987. A year later, the Western League absorbed the Southern Junior D Hockey League. They operated under the Western moniker for three more years.
In 1991, the Western League was dissolved and the OHA Junior Development League was created. At this time, the Applejacks turned into a team to reckon with.
In the early years of the OHAJDL, the league was dominated by the Thamesford Trojans and Lucan Irish, but come the 1995-96 season the Applejacks made their first finals appearance of what would be four consecutive years.
In the 1996 OHA Cup Finals, the Applejacks fell to the Exeter Hawks 4-games-to-3. This came after finishing 2nd place in the entire league with 27 wins.
The 1996-97 season had the Applejacks finish second again with 28 wins, but lose in the OHA Cup final 4-games-to-none to the Mount Brydges Bulldogs.
The 1997-98 season was one for the ages for the Applejacks. They finished first in the OHAJDL with 28 wins and made it all the way to the league final for the third straight year. They defeated the Exeter Hawks 4-games-to-3 to win their first OHA Cup.
The 1998-99 season, the Applejacks again finished first in the league with 30 wins. In the playoff they made it to the league final for the fourth straight year only to lose 4-games-to-3 to the Lucan Irish.
In 2000-01, the Wellesley Applejacks found their footing again. They finished fifth in the OHAJDL with 25 wins and made it to the OHA Cup final again. This time they lost 4-games-to-1 to the Mount Brydges Bulldogs.
In 2002-03, the Applejacks finished the season in 8th place with 19 wins. They surprised the league and made it to the league finals again. Wellesley ended up getting swept by the Thamesford Trojans 4-games-to-none.
In 2006, the OHAJDL was dissolved and the Applejacks joined the Southern Ontario Junior Hockey League — whoch was promoted to Junior C officially in 2012.
In the Summer of 2013, the Ontario Hockey Association realigned the leagues and the Applejacks ended up in the new Midwestern Junior C Hockey League.
During the 2018-19 season, Wellesley claimed the Doherty Division title over the Tavistock Braves.
In the 2022-23 season, Wellesley emerged as the Doherty Division champions, defeating the New Hamburg Firebirds. Their triumphant journey continued with a best-of-seven series against the Glanbrook Rangers, securing a remarkable 4-1 series win, thus earning them the distinguished title of South Conference Champions. This achievement paved their way to a round-robin tournament for the Schmalz Cup.
In a thrilling turn of events, the Applejacks secured an electrifying overtime victory against the Lakeshore Canadians in the Semi-Finals, propelling them into the Schmalz Cup Final. There, they faced the Clarignton Eagles, the reigning champions. In a fiercely contested match, Wellesley emerged victorious with a score of 7-5, marking a historic moment for the organization as they claimed their first-ever Schmalz Cup Championship.
Wellesley Apple Jacks Season-by-season record
|27||2013-14||39||19||17||–||3||197||148||41||5th MWJCHL||Lost Quarters – 3-4 – (Merchants)|
|28||2014-15||40||13||27||0||–||117||166||26||8th MWJCHL||Lost Quarters – 0-4 – (Centennials)|
|29||2015-16||40||21||17||2||–||149||152||44||4th of 8 MWJCHL||Won Quarters – 4-1 – (Braves)
Lost Semifinals 0-4 (Centennials)