Challenge Cup pros

Tennis Pros Justin Chaffee (Bridgton Highlands) and Chris Chaffee (Jackson Club) with the Challenge Cup.

Bridgton Highlands won the 2026 Challenge Cup against Jackson Tennis Club this past Saturday, Aug. 8, at the Jackson Club. Jackson was looking for their seventh consecutive win, but Bridgton rallied to capture the cup and will proudly host the event next year.

The Challenge Cup originated when Justin Chaffee and his twin brother, Chris, were tennis pros working together at Onteora Club in upstate New York. Inspired by the three-day “Owl matches” played there, the brothers decided to create a playoff between the clubs where they are tennis pros. This tournament offers a wonderful opportunity for players to connect with both new and familiar faces.

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