Ryan Dunne (FREDDIE PRINZE, JR.) has lived in Cape Cod all of his life, where he's watched various young men play in the summer baseball league, hoping to impress professional major league scouts. Now, along with catcher Billy Brubaker (MATTHEW LILLARD), hotshot competing pitcher Eric Van Leemer (COREY PEARSON), and fellow players Miles Dalrymple (MARC BLUCAS) and Mickey "Domo" Dominguez (WILMER VALDERRAMA), Ryan is taking his one last shot at playing professional ball.
Accordingly, and when not fooling around with the promiscuous Dede Mulligan (BRITTANY MURPHY), mowing lawns for his father, Sean (FRED WARD) and his lawn service, or hanging out with his friends Auggie (GABRIEL MANN) and Pete (JED ROBERT RHEIN) at the local bar where his brother, Mike (JASON GEDRICK) works serving drinks, Ryan tries to impress the Chatham A's coach, John Schiffner (BRIAN DENNEHY).
Known equally for his skill as well as his inconsistent nature coupled with a reputation for being hotheaded on the mound, Ryan has his work cut out for him. The same holds true when he finds himself attracted to Tenley Parrish (JESSICA BIEL), the pretty daughter of Rand Parrish (BRUCE DAVISON), a wealthy lawn client who doesn't approve of their romance due to their class differences.
As the season begins and a professional scout (JOHN C. McGINLEY) observes his game, Ryan tries to prove his worth both on and off the diamond, all while dealing with both internal and external obstacles that might derail both his personal and professional aspirations.