2020: Inaugural season The league was formed by the
Portland Pickles in 2020 following the cancellation of the
West Coast League's regular season due to the
COVID-19 pandemic. Months prior, the Pickles also founded a developmental farm club of their own known as the
Portland Gherkins. The Pickles and Gherkins were joined by the previously independent
Gresham GreyWolves and West Linn Knights and played the inaugural two-week season at
Bob Brack Stadium in
Aurora, Oregon, with all players, coaches and staffs having to follow the COVID-19 guidelines at the local, state and federal levels and limited fans in attendance. The league even grabbed the attention nationally of
Forbes magazine. Play officially began on July 11, 2020, with the Pickles playing the Gherkins. On July 15, 2020, the league suspended play for at least seven days following positive COVID-19 tests from two players, just four days after the inaugural season started. The league would resume play eight days later. The Knights won the inaugural league championship, defeating the Pickles 8–7 in the championship game.
2021 The league was so successful that it announced a second season and that all of its games would be moved to
Walker Stadium at Lents Park in southeast Portland, home of the Pickles, who returned to the WCL. The Knights were folded and both were replaced by the revived
Portland Rosebuds (named for the former
Negro league team from the 1940's) and
Willamette Wild Bills. The Rosebuds won the 2nd WWWL Championship defeating the Wild Bills 6–4 in the finals.
2022 The league announced expansion into
Cleburne, Texas, with a newly-formed four-team Texas Division with all games being played at
The Depot at Cleburne Station, also the home of the
Cleburne Railroaders of the professional
American Association. The four teams founded by the league included the Cleburne Eagles (named for the former
Negro league team from the 1930's to 1960's), Joshua Trees, Burleson Boxers and Fort Worth Rodeo Cats. However, the teams never played due to lack of interest. Therefore, the Texas Division teams and plans were scrapped by the league. The Oregon teams all returned for a third season and became known as the Portland Division with all games once again being played at Walker Stadium. The Portland Gherkins won the 2022 WWWL Championship defeating the Gresham GreyWolves 9–7 in the championship game.
2023 On April 13, 2023, the league announced that they would play a fourth season. On August 26, the Willamette Wild Bills won their first WWWL Championship by beating the defending champion Gherkins 9-8 to capture the title. In 2024, the WWWL went dormant.
2025 After taking a season off, the WWWL returned to action with all of its teams playing the Pickles in pre-season non-league action. ==Special rules==