Despite wind gusts surpassing 30 mph throughout the day in Kapalua, HI., Woodland - who won the 2018 Waste Management Open to receive an invite to this week's event - managed to string together five consecutive birdies on the Plantation Course's back nine to sit at 12-under through two rounds.
McIlroy and DeChambeau both shot 5-under rounds of 68 to lead the group chasing Woodland. First-round leader Kevin Tway also sits at 9-under.
Defending champion Dustin Johnson was one back heading into Friday's round, however, a costly two-stroke penalty on No. 4 derailed his round. He ended up shooting a 1-over 74 to snap his under-par streak at the Tournament of Champions at 32 rounds.