A highly regarded prospect out of Costal Carolina University, Woodward was picked in the 15th round of the 2010 MLB draft by the Oakland A's, but opted to return to school for his senior year. The move paid off as the left-handed hitter was named the Big South Conference All-Star Third Baseman following a final collegiate season hitting .342 with four homers, 37 RBI and 31 steals. He also walked 35 times and was hit by 22 pitches, leading to a .480 on-base percentage. Those numbers earned Woodward a seventh round selection in the 2011 draft by the Los Angeles Dodgers.

As a junior for the Chanticleers, Woodward hit .324 with five homers and 35 RBI. Additionally he swiped 55 bases in 64 games, ranking second in NCAA Division-I while helping to lead Coastal Carolina to a 55-10 record overall including a perfect 25-0 Big South mark. The season culminated with an appearance in the College World Series Super Regionals. Furthermore, he was honored as the Big South Conference All-Star Third Baseman.

Woodward burst onto the scene as a freshman in 2008 collecting First Team Freshman All-America honors as well as Big South Conference All-Star Third Baseman and Big South Freshman of the Year accolades as he hit .364 with seven homers and 45 RBI. He finished fifth in the nation with 42 stolen bases and was sixth with 58 walks against only 40 strikeouts. Also, the Markle, IN native was hit by 30 pitches, resulting in a .540 on-base percentage that ranked fourth nationally.

For his collegiate career, Woodward hit .333 with a .486 OBP. He stole 158 bases while only being caught 24 times. He finished in the top 10 of the NCAA stolen base leaders in three of four seasons with the Chanticleers.

Woodward most recently played in 2011 for the Ogden Raptors (Pioneer - Rookie). In 36 games he scored 25 runs with a .219 batting average, four long balls and 12 driven in.