A new OJCLL began operation in 2008 with five teams (Caledon Bandits, Centre Wellington Warlords, Innisfil Wolfpack, Shelburne Vets, West Durham Patriots).

The 2011 season saw a huge change in the league as it expanded from eight teams with the addition of Halton Hills, Hamilton, Mimico and Wilmot in the west.

The Huntsville Hawks would also drop down from Junior "B" to join the league while the Centre Wellington Warlords ownership changed and were rebranded as the Fergus Thistles.

In 2013 the league would stay the same in the number of teams at 16 however there would be a new champion crowned as the Halton Hills Bulldogs took the title in an overtime thriller in Cornwall defeating the three time champs from Clarington 11–10.

In 2014 the league lost another eastern team as Brockville Ballistic ceased operations while the Oakville Hawks and the Six Nations Warriors came in.

The league switched back to an East-West division format which saw the Cornwall Celtics defeat the defending champions from Halton Hills 3–0 to win their first title.

The 2015 West champion Warriors dropped to third in the regular season standings while Wilmot Wild and the Fergus Thistles tied for top spot with identical 14–2 records.

In what will go down as one of the most tightly contested playoff series in league history, the Shamrox would eventually eke out a 4–3 win in Game 5 in front of a packed Garnett B. Rickard Arena in Clarington.

2023 ushered in change for the OJCLL, with Barrie's Jim Lowe taking over the role of commissioner from Reg Hollinshead, who was elected Vice-President Junior to Major Lacrosse for the OLA.

A off-season dispute between the OLA and FCQ resulted in the operating agreement that had permitted the Kodiaks and the Centurions to compete in the league.

A subsequent agreement provided OLA membership to the Kodiaks for 2024 and 2025, ensuring that the team could attempt to defend its 2023 Meredith Cup Championship.