The Toronto Blue Jays selected Woodward in the 54th round of the 1994 Major League Baseball draft. He made his major league debut on June 7, 1999, hitting a sacrifice fly in an 8-2 loss to the New York Mets. From 2002 through 2004, Woodward was the starting shortstop in about half of Toronto's games. On August 7, 2002, he achieved a rare feat by hitting three home runs in one game as a shortstop. After an injury-plagued and difficult offensive season in 2004, the Blue Jays released him.
New York Mets
In 2005, Woodward signed with the New York Mets. 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. In 2006, he struggled with injuries and the Mets chose not to re-sign him.
Atlanta Braves
On December 20, 2006, Woodward agreed to a one-year deal with the Atlanta Braves. He went through a huge down season in Atlanta however, hitting an MLB-position player worst.199 with only one homer.
Yankees, Phillies, and Brewers
On February 8, 2008, Woodward signed a minor league contract with the New York Yankees then was released on March 26 and signed with the Philadelphia Phillies on March 28, 2008, where he was assigned to the Phillies' Triple-A affiliate, the Lehigh Valley IronPigs. On May 2, 2008 Woodward was released. He signed a minor league contract with the Milwaukee Brewers on May 31, 2008, and was assigned to Triple-A Nashville. He became a free agent following the season.
On August 7, Woodward was claimed off waivers by the Boston Red Sox only to be designated for assignment eight days later on August 15, due to the acquisition of Álex González. He was later optioned to the Triple-A Pawtucket Red Sox and would be called up in September when rosters expanded.
Second stint with the Mariners
Woodward and the Seattle Mariners reached an agreement on a minor league contract with an invitation to spring training on January 6, 2010.
Second stint with the Blue Jays
On March 14, 2011, Woodward signed a minor league contract with the Toronto Blue Jays. Woodward was called up by the Blue Jays organization on April 21, 2011. He was outrighted to the minors on April 28. He returned to the team on September 4 for the remainder of the season. For the season, he was hitless and did not reach base in ten at bats. He was named a 2011 MILB.COM Toronto Organization All Star, after batting 296/.353/.474 with 13 home runs in 422 at bats in AAA for the Las Vegas 51s. 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. On April 3, Woodward was assigned to the Las Vegas 51s. With them, in 2012 he batted.285/.338/.392 with 2 home runs, 34 RBIs, and 4 stolen bases in 309 at bats.
Coaching
Mariners
Woodward retired on November 1, 2012 and joined the Seattle Mariners organization as minor league infield coordinator. He became the Mariners' infield coach in 2014, and served as the Mariners first base coach in 2015, but opted not to return for the 2016 season after manager Lloyd McClendon was fired.
Dodgers
On December 17, 2015, he was named the third base coach for the Los Angeles Dodgers. He spent the 2016 through 2018 seasons in that position. Woodward managed New Zealand in the 2017 World Baseball Classic qualification tournament in Australia in 2016. Woodward interviewed for the New York Yankees manager position after the 2017 season, which eventually went to Aaron Boone.
Managerial career
Texas Rangers
On November 2, 2018, Woodward agreed to a three-year contract to be the manager of the Texas Rangers beginning with the 2019 season.
Managerial record
Personal life
Woodward is married to Erin Woodward, with whom he has three children. He met his wife, a native of Aurora, Ontario, while playing with the Toronto Blue Jays. He resides in Chandler, Arizona. In 2004, Woodward was featured in an episode of .
