The Red Sox completed the "three-peat" in 2016, led by a sterling playoff performance by University of Maryland infielder Kevin Smith. The club met Orleans in the opening round of the playoffs, and took Game 1 with a 4–2 win marked by a mammoth blast by Smith. The Sox completed the sweep in Game 2 at Eldredge Park, taking a tight 2–1 ballgame on the strength of a second-inning dinger by Cape Cod native Will Toffey, and an eighth-inning RBI by Joey Thomas. The win set up an East Division finals match with Chatham. Smith homered again in Game 1 at Red Wilson Field, and Y-D took the slugfest, 9–8. The Sox completed their second series sweep in Game 2 on the road, getting six effective innings by starter William Montgomery, and prevailing by a 4–1 tally, sending the Sox to a title series match against Falmouth. The Sox fell to Falmouth, 5–4, in the Game 1 opener at Guv Fuller Field. In Game 2 at home, Y-D jumped out to a 3–0 lead in the first on back-to-back homers by Toffey and Deon Stafford, Jr., and got a two-run clout in the fourth by Smith, knotting the series with a 9–4 win. The Sox went up on the Commodores early in Game 3, scoring three runs in the first two innings to take a 3–0 lead. Starter Bryan Sammons tossed six-plus shutout innings of two-hit baseball to make the score hold up as the final tally, the win earning the Red Sox their third consecutive league title. Smith was awarded playoff MVP honors, having batted .370 with three homers in the playoffs. His sixth league championship, the 2016 title tied Scott Pickler with Falmouth's Bill Livesey for CCBL career championships by a manager. Pickler was inducted into the CCBL Hall of Fame in 2019.