Before coming to the majors, Woodling was a four-time minor league batting champion. He mostly played left field when he entered the majors after his time in the U.S. Navy, but spent much time in right field and also played ninety-three games in center.
Woodling played with many teams during his career, the longest term of service being with the Yankees for six years. With them, Woodling had what was probably his best year, 1953. Although he only had 395 at bats, he led the American League with a .429 on-base percentage.
While Woodling was with the Yankees, the team won five consecutive World Series (1949–1953). During that time, Yankee managerCasey Stengel praised the outfielder's ability to run and throw. Stengel generally platooned him with right-hander Hank Bauer, but each averaged 400 at bats per season. Woodling hit a solo home run in each World Series from 1951 through 1953, and, in 1951, helped Allie Reynolds secure his first of two no-hitters on the season, when he homered in a 1–0 win over Bob Feller and the Indians. In 1952, Woodling became the first player to pinch-hit a triple in the World Series.
On November 17, 1954, a record seventeen-player deal took place between the Orioles and Yankees, involving Woodling, future twenty-game winner Bob Turley and Don Larsen, who would go on to pitch a perfect game in the 1956 World Series for New York. Woodling had been sidelined for the last part of the 1954 season with a broken arm.
Soon, Woodling moved to the Indians where he set career-highs in home runs (19), runs batted in (78), and batting (.321) in 1957. A few months before he turned forty, he was sent to the New York Mets, where old Yankees manager Casey Stengel was working on his latest project, the newborn Mets. Woodling would be managed by Stengel for the remainder of the 1962 season. He was released before the 1963 season, after publicly criticizing the front office's contract negotiations with Marv Throneberry.