[2] This early Cape League operated through the 1939 season and disbanded in 1940, due in large part to the difficulty of securing ongoing funding during the Great Depression.

[12][13][14][15] In all three seasons of the joint Chatham-Harwich team, the club featured Boston College batterymates pitcher Pete Herman and catcher George Colbert, as well as flashy infielder Artie Gore.

Chatham continued to be managed by John Carroll, whose 1963 club featured CCBL Hall of Famer Ken Voges of Texas Lutheran University, who led the league with an astronomical .505 batting average.

[27] The Red Sox finished the regular season with a 28–6 record, good enough for first place in the Lower Cape Division, but fell to Orleans in the playoffs.

[28][29] Lefebvre's team featured CCBL Hall of Fame second baseman Steve Saradnik of Providence College, who batted .314,[30] and pitcher Charlie Hough, who went on to a 25-year major league knuckleballing career.

[31][32][33] Lewis' 1965 squad returned Saradnik, and added another two CCBL Hall of Famers in University of Connecticut righty Ed Baird, who posted a 3–0 record with a 0.45 ERA,[34] and George Greer, who batted .349 and led the league in doubles and triples.

[35] The star-studded 1966 Chatham team returned Saradnik, Baird and Greer,[36][37] and added another three CCBL Hall of Famers: catcher Tom Weir, who led the league with a .420 batting average,[38] all-star hurler Joe Jabar, who went 7–0 with a 1.53 ERA and took home the league's Outstanding Pitcher Award,[34] and Pittsfield, Massachusetts native Tom Grieve.

[45] Munson was inducted into the CCBL Hall of Fame as part of its inaugural class of 2000, and his name graces the league's annual award for batting champion.

[61] The 1985 A's returned to the league championship series behind the play of CCBL Hall of Famers Tim McIntosh and Mark Petkovsek, but were shut down by Cotuit.

Skipper Rich Hill's 1992 Chatham squad posted an impressive 31–11 regular season record, and featured ace reliever Scott Smith and CCBL Hall of Fame hurler Steve Duda.

Chatham played small-ball in the top of the 12th, pushing across Jeremy Carr, who had walked and reached third on a stolen base and a Cotuit error, then scored on a Brian Garrett single.

[74] In 1996, Chatham featured the league's Outstanding Pro Prospect, fireballing reliever Matt Anderson, but the team struggled early on, losing eight in a row at one point.

In Game 1, Chatham's Matt Purkiss clobbered a two-run homer in the third and ace Keith Evans worked 11 innings allowing only four hits as the A's and Whitecaps took a 2–2 tie into the 12th.

In the top of the 12th, Chatham's Scott Friedholm smashed a three-run homer to left, and Anderson came on in the bottom half of the frame to nail down the victory.

Chatham completed the sweep with a 3–0 win in Game 2 on the strength of second baseman Jermaine Clark's two-run double, and advanced to the title series against Falmouth.

[75] The 1996 championship series opened at Guv Fuller Field, with Chatham catcher Scott Fitzgerald stifling the Falmouth attack early on in Game 1, cutting down three stolen base attempts in the first three innings.

Chatham pushed across three runs playing small-ball and A's starter Seth Etherton was masterful, twirling eight shutout innings and striking out 14 before turning it over to Anderson for the ninth-inning save in the A's 3–0 win.

Clark, whom Schiffner described as the team's spark plug all season,[76] went 3-for-4 with a pair of doubles to go with his usual stellar work in the field, and the A's downed the Commodores, 6–2, for the title.

Evans and Clark shared playoff MVP honors as Chatham sealed its fourth Cape League championship and its first to be clinched at Veterans Field.

Game 3 at Wareham was a classic pitcher's duel as Currier was matched up against CCBL Hall of Famer and future major league all-star Ben Sheets for the Gatemen.

The A's evened the series again in Game 4 at home, taking the lead in the bottom of the eighth on RBIs by Ryan Earey and Barry Gauch, and hanging on to win, 4–3.

[81] Behind the solid mound-work of Devon Nicholson, Chatham clung to a 3–1 lead through seven in a tense Game 5 finale that saw Gatemen skipper Don Reed tossed in the seventh.

Currier was joined on the staff by CCBL Hall of Famer Derrick DePriest, who did not allow an earned run in 22.2 innings of work, and was named the league's Outstanding Relief Pitcher.

[113][114][115] Assistant coach Todd Shelton was named interim manager on July 28, and led the team to a 5-1 record over its final six games, highlighted by a four-game winning streak to end the season.

After being drafted and playing part of a minor league season in the Pittsburgh Pirates organization in 1977, Schiffner returned to the Cape as an Assistant Coach in Harwich for the summer.

Jim Collins' The Last Best League (2004, ISBN 0-306-81418-8) is a non-fiction account of the 2002 Chatham A's, which featured infielder Jamie D'Antona and manager John Schiffner as the book's protagonists.

Collins follows and recounts every move the players, coaches, fans, and others make in the ethnographic account of the full 2002 Cape Cod Baseball League and Chatham A's season.

D'Antona, a highly touted power hitter from Wake Forest University who quickly becomes Collins' primary player focus in the book, is depicted as a laid-back ballplayer whose potential is hindered by occasional lapses in judgment and lack of effort.

Following a short Major League career and a stint playing professionally in Japan, D'Antona returned to Chatham as the Anglers' hitting coach in 2017, working under John Schiffner in his final season as A's manager.

He was selected fourth overall by the San Diego Padres in the 2003 MLB Draft based largely off his performance on Cape Cod, and pitched in the Major Leagues for 10 seasons.