Boddicker's pitching repertoire, once called "Little League slop" by Rod Carew, featured off-speed pitches and deception to compensate for a lack of power. He was able to throw from three different arm angles. He had a fastball that never came close to reaching 90 miles per hour. The one pitch that made him famous was the fosh, which he called "a glorified changeup." Another one he used with success was the slurve. Tony Phillips once commented, "What I noticed about him is that he lets you get yourself out. I find myself sometimes actually jumping at his pitches, being overanxious because he doesn't throw very fast, and I wind up popping the ball up."
Boddicker had a W-L record of 134-116 with a 3.80 ERA during his career. His best season was 1984 when he went 20-11 with a 2.79 ERA (leading the American League in both wins and ERA). He also won the Gold Glove Award in 1990.
In the 1983 postseason with the Baltimore Orioles, Boddicker pitched brilliantly. With his team down 1-0 in both the ALCS and World Series, Boddicker pitched his team out of the hole by winning Game 2 of the ALCS 4-0 vs the Chicago White Sox (complete game shutout) and Game 2 of the World Series 4-1 vs the Philadelphia Phillies en route to a world championship.
On July 29, 1988, Boddicker was traded from the Orioles to the Boston Red Sox for OF Brady Anderson and pitcher Curt Schilling. Boddicker went 7-3 down the stretch for the Sox, helping them win the AL East crown that year. He went 15-11 in 1989 and had a stellar season in 1990, going 17-8 with a 3.36 ERA while helping the Red Sox win another division title.
After signing with the Royals, he finished 12-12 with a 4.08 ERA in 1991, his last full season (30 games). After his contract was purchased by the Brewers, he pitched 54 innings for them in 1993, his final year. He finished 3-5 with a 5.67 ERA that year.