From its founding in 2005, the Champions of The Wiffle®Ball Championship have received gold medals to commemorate their accomplishment.  In 2010, in conjunction with the celebration of New Carlisle's 175th anniversary, Hometown Days commissioned a traveling trophy to be awarded annually to the Champions of Wiffle®ball. Several historical names were considered for the trophy, including naming it after the town's founder Richard Carlisle, before settling on the Hometown Cup.

After unexpected delays in the production of the trophy, it was first awarded a few weeks after the 2010 Championship to Where My Pitches At? in a special ceremony on team member Sam Zucker's front porch. In subsequent years, the trophy has been presented to the champions immediately after their medals and is featured prominently in the official Championship photo in front of the Migley Field marquee.

The Hometown Cup has been referred to as the "Stanley Cup of Wiffle®Ball." Each Championship team name, along with the names of every individual player, are engraved on the base of the trophy. Unlike its hockey counterpart, previous engraving errors have been corrected to accurately reflect the history of the champions.

Champions agree to return the trophy prior to the next year's Championship. As is tradition, the safe return of the Cup is accepted as the defending champions' entry fee into the following tournament. Champions are also honored with a banner that hangs from Champions Field and Migley Field during the tournament.

The trophy is available on Saturday during pool play for photo opportunities.