Chatham has won five Cape Cod Baseball League Championships in the modern era (since 1963): 1967, 1982, 1992, 1996 and 1998. In those 50 seasons, Chatham has reached the postseason 31 times, while capturing 16 regular season titles and 18 division championships. The team has reached the 30-win plateau four times, including back-to-back seasons in 1966 and the title year of '67.

Chatham counts more major league alumni (142 as of July 23, 2012) than any other CCBL team, and more alumni in the CCBL Hall of Fame than any other club (25). Two of the top three managers in CCBL history coached for Chatham: Ed Lyons with 331 wins (1976-82) and John Schiffner 460 wins (as of 2013).

Three Chatham players have won the CCBL's Pat Sorenti Award for regular season MVP: Thurman Munson ('67), Joey Cora ('84) and Evan Longoria ('05). Eleven times has a Chatham pitcher won the B.F.C. Whitehouse Award for the CCBL's most outstanding pitcher, seven Chatham players have been given the Robert A. McNeece Award for most outstanding pro prospect, and seven Chatham players have won the league's batting title, including Thurman Munson (for whom the award is named) in '67.