[10] 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.

[21] In 1958, undefeated world heavyweight champion and Brockton, Massachusetts native Rocky Marciano was in the stands to cheer on his younger brother Pete, who played catcher for Brewster.

He posted a .772 slugging percentage, and missed capturing the league's triple crown by just two points, his .359 average falling just shy of Chuck Knoblauch's .361 mark.

[33] Brewster's 1992 team starred CCBL Hall of Fame pitcher Billy Wagner, who fanned 79 batters in 44.1 innings of work, and was named the league's Outstanding Pro Prospect.

[34][35] Whitecap players took home hardware as East Division MVP's of the CCBL All-Star Game in three consecutive seasons, as Will Scalzitti claimed the honors in 1991, Wagner in 1992,[36] and Geoff Blum in 1993.

Manager Bill Mosiello's 1994 Whitecaps squad starred CCBL Hall of Famer Sean Casey, who hit .338 with 40 RBI, and led all first basemen with a .993 fielding percentage.

The 1998 Whitecaps featured future major league all-star Chase Utley and CCBL Hall of Famer Bobby Kielty.

In Game 1 at Cape Tech, Whitecap lefty hurler Ryan Olson kept the Mets at bay through eight innings, allowing only five hits.

[42] Behind the solid work of starter Mike Wodnicki in Game 2, Brewster combined a mix of bunts, walks and stolen bases to build an early 5–0 lead on a drizzly day in Hyannis.

Playoff MVP honors went to Brewster's Jack Headley, who made a key catch in the field to preserve the Game 1 victory, and went 5-for-18 at the plate in the title series.

Macaluso's 2003 club finished in first place in the East Division and featured league Outstanding Relief Pitcher Jarrett Santos and CCBL Hall of Famer J.C. Holt.

[46] The Whitecaps came home to Brewster in 2006, as a grant from the Yawkey Foundation and matching funds from the team allowed for the construction of a field behind Stony Brook Elementary School.

[47][48] The 2006 team featured CCBL Hall of Famer Shaun Seibert, who posted a 6–0 record with a microscopic 0.39 ERA and was co-recipient of the league's Outstanding Pitcher Award.

Whitecaps starter Will Tribucher twirled six and two-thirds shutout innings, and Hunter Bishop delivered the decisive blow, hammering his third home run of the playoffs to put Brewster up 2–0 in the sixth.

The score was preserved by a diving catch on the warning track by Costes with the bases loaded and two outs in the top of the seventh, and Brewster hung on to win by the 2–0 tally to secure its second league championship.

[59] The 2020 CCBL season was cancelled due to the coronavirus pandemic,[60] and the Whitecaps were dealt an additional blow as former skipper John Altobelli was among the nine killed in the helicopter crash that claimed the life of NBA legend Kobe Bryant.

In Game 1 at home, Brewster outfielder Chad Castillo went 3-for-4 with a double and two RBIs that accounted for all the scoring as Whitecap hurlers Brian Fitzpatrick, Michael Prosecky and closer Dale Stanavich combined for the 2–0 shutout win.

With the bases full of Whitecaps, a balk call brought in the go-ahead run, and Stanavich came on in the bottom of the inning to strike out the side and send Brewster to the CCBL title series.

[66][67] Hoping to complete the series sweep in Game 2 at Stony Brook Field, Brewster trailed early, 5–0, after a Bourne first-inning explosion.

With the score knotted at 6–6 after six, Bullard blasted a home run to lead off a four-run Caps seventh, and Brewster held on to clinch the championship with a 10–6 win.