First up, a stunning upset! Bottom-seeded Westhampton/WHB kicked top-seeded Montauk's butt good and hard in the first contest. Many suspect this is a protest vote against Montauk rather than genuine love for Westhampton; we shall see in its next contest, which will be against Water Mill.
It was a close battle between Springs (8) and Water Mill (9), with Water Mill squeaking into a win by four votes. Next up, East Hampton (5) fairly easily defeated scrappy little North Haven (12). There's always next year, North Haven!
Mighty Bridgehampton (4) was the winner against long shot Northwest Woods (13). Bridgehampton will square off against East Hampton next week. After that, Sagaponack (11) narrowly defeated always-popular Southampton (6). Better luck next year, Southampton.
Sizzling hot Sag Harbor (3), the winner of several past Cups, easily won against Shelter Island (14). Can Sag Harbor rout Sagaponack next week in the battle of the Sags?
Finally, Hamptons Bays (7) blew away Wainscott (10). Is this Hampton Bays' year? It will face off against past Cup winner Amagansett (2) next week, which defeated Quogue/East Quogue (15).
Curbed Cup fever: catch it next week!