He played in MLB for the Toronto Blue Jays, New York Mets, Atlanta Braves, Seattle Mariners, and Boston Red Sox, from 1999 through 2012.

He made his major league debut on June 7, 1999, hitting a sacrifice fly in an 8–2 loss to the New York Mets.

On August 7, 2002, he achieved a rare feat by hitting three home runs in one game as a shortstop (the first as a Blue Jay and the 15th overall).

Woodward was the epitome of flexibility, playing at seven different positions including the entire infield and performing well off the bench and as a starter and even managed two game-winning hits.

[5] On June 19, 2009, Woodward was called up from the Triple-A Tacoma Rainiers after second baseman José López was placed on the bereavement list.

[6] He made his debut for the Mariners that night, in their 4–3 win against the Arizona Diamondbacks, he was 2 for 4 in that game with a stolen base and a run scored.

On August 4, Woodward was designated for assignment to make way for Adrián Beltré who was activated from the 15-day disabled list the same day.

Woodward and the Seattle Mariners reached an agreement on a minor league contract with an invitation to spring training on January 6, 2010.

[14] He became a free agent after the season, and re-signed to a minor league contract for 2012 by the Toronto Blue Jays, who invited him to spring training.

[11] Woodward retired on November 1, 2012 and joined the Seattle Mariners organization as minor league infield coordinator.

[24] On January 20, 2023, Woodward was hired by the Dodgers as a special assistant in the front office as well as a roving infield instructor for their organization.