Sutcliffe broke into the majors in 1979. He won 17 games for the Los Angeles Dodgers and was the first of four consecutive Rookies of the Year for the Dodgers from 1979–1982 (Steve Howe, Fernando Valenzuela, and Steve Sax were the others). The Dodgers traded Sutcliffe to the Cleveland Indians for Jorge Orta, a journeyman outfielder.

Sutcliffe won 31 games over the course of the next two seasons for Cleveland and led the American League in earned run average in 1982. In mid-1984, Cleveland traded a struggling Sutcliffe to the Chicago Cubs for Mel Hall and Joe Carter. Sutcliffe rebounded and won 16 games for the Cubs while losing only one, helping them to the division championship.

Rick won the Cy Young Award with a unanimous vote. He also finished fourth in the league MVP voting. When he re-signed with the Cubs as a free agent the following year, his contract briefly made him the highest-paid pitcher in baseball.

Recurring arm injuries caused Sutcliffe to miss most of the 1990 and 1991 seasons and the Cubs did not offer him a contract for the next season. Signing with the Baltimore Orioles, Sutcliffe went 16–15 and 10–10 in 1992 and 1993, starting the first game at Oriole Park at Camden Yards. He wound up his career with the St. Louis Cardinals in 1994, going 6-4 in an injury-plagued season. He retired with a career record of 171–139, with an ERA of 4.08. He holds the unique distinction of having won each of the following league awards, once each, and each in a different season: Rookie of the Year (1979), Cy Young Award (1984), ERA leader (1982), and wins leader (1987).

After his retirement from baseball, Sutcliffe became a color commentator for the San Diego Padres on Channel 4 San Diego (1997–2004), ESPN (1998–present) and DirecTV/MLB International (1997–2002 and since 2010, as well as a minor-league pitching coach in the San Diego Padres system for a couple of seasons. He also broadcasts the World Series and either the ALCS or NLCS for MLB International, where he is teamed with Gary Thorne. In previous years he has also appeared with Dave O'Brien.

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