Named for the original John Deere model tractor, the Waterloo Boys are among the oldest teams in the Grain Belt Association, a low-A minor league. The Boys' affiliation with the Greens dates from 1994, when the Timbers moved from Seattle and planted themselves along the Rock River in Moline. Waterloo has never reached the postseason in that time, though through its clubhouse doors have passed some of the best of the current Moline stars, including Andruw Jones and Kris Benson.

The team is named after the Waterloo Boy, a John Deere tractor produced in the early years of the last century. In 1911, under Deere & Company's third president, William Butterworth, six noncompeting farm equipment companies were brought into the Deere organization, establishing the company as a full-line manufacturer of farm equipment. In 1918, Deere & Company purchased the Waterloo Gasoline Traction Engine Company in Waterloo, Iowa, and tractors became an important part of the John Deere line. The "Waterloo Boy" was produced until 1923, when Deere introduced its "Model D," one of the most popular tractors ever built.