Pickler's first title came in 2004, when the team rolled through the playoffs, sweeping Brewster in the semi-finals, and sweeping Falmouth in the finals. The Red Sox took Game 1 of the title series at home, 4–3, on shortstop Ryan Rohlinger's game-winning 8th inning homer. Game 2 of the finals was an all-time classic, with the Sox coming back to tie the game at Guv Fuller Field in the ninth inning on an RBI by CCBL Outstanding New England Player Award winner Frank Curreri. With two outs and the bases loaded in the bottom of the tenth, Y-D outfielder Jim Rapaport made a game-saving diving catch on a sinking liner to right. In the top of the 11th, Y-D opened it up with four runs, including a two-run bomb by Nick Moresi, to secure the 8–4 victory and claim the league crown. Y-D was led by playoff co-MVPs Rohlinger and pitcher Joshua Faiola. Rohlinger hit .429 in the postseason, including a key squeeze bunt in the 11th inning of the Game 2 finale. Faiola earned the save in Game 1 of the finals, then got the win in Game 2, pitching two innings of scoreless relief.