The Tiverton Wiffleball League's origins go back to 1996, when kids from Hurst Lane and Watuppa Avenue started keeping official scorebooks of their summer pick up wiffleball games. They'd usually play 4 or 5 days per week in the Anselmo's yard during summer vacation.
With the kids all grown up, in April of 2011, the Tiverton Wiffleball League was officially formed. During that first season, new teams were chosen every week using a classic school yard pick, but every player's stats were recorded on an individual basis. Over 60 people played during the inaugural season, with 21 of them showing up regularly. After the success of its inaugural season, the Tiveron Wiffleball League formed 3 permanent teams for the start of its 2012 season. The Hurst Lane Orioles, Watuppa Pirates, and Garden Heights Brewers. With consistant teams for the entire season, competition grew and The 2012 season was an even greater success with the Watuppa Pirates winning the first ever Aguiar Cup.
With a growing amount of interest, the Tiverton Wiffleball League expanded in 2013 with the addition of a fourth team, the Hayden Ave Astos. At the conclusion of the 2013 season, the Garden Heights Brewers folded and a new team, the Robert Grey Padres were formed.
The 2014 season will see another new team added to the league, the Colonial Athletics.