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The rivalry between the Detroit Grape Chews and the Milwaukee Flamingos is a long and complicated one. Starting in Season 1 of the Hellmouth Cup, the rivalry was intense and white-hot; it was named as one of the three Crown Jewels of Golly rivalries. On-field fistfights during Grape Chews-Flamingos matches were more intense and resulted in far more injuries than fistfights between the Grape Chews and any other teams.

However, as the Hellmouth Cup progressed, the rivalry became much more one-way, with the Detroit Grape Chews building much of their team identity around the rivalry, but the Milwaukee Flamingos rapidly losing interest in the rivalry. The Flamingos cited a desire to establish their own identity as a benevolent flock of birds, and began to publicly distance themselves from the Grape Chews. (It is a well-known fact that Milwaukee Flamingos players have never gotten into a single fistfight outside of their matches with the Detroit Grape Chews.)