The 51-year-old Wood birdied the last two holes for a 6-under 66 and won by a stroke when Glasson bogeyed the final hole. Wood played 54 holes without a bogey, finishing at 14-under 202 at Kapolei Golf Course.
"I had a great back nine," Wood said. "I just hung in there and the putts kept continuing to fall, and I got a little bit lucky with the way Bill finished. ... I knew Bill would have to help us out some."
Five strokes behind Glasson entering the round, Wood chipped to 5 feet to set up his birdie on the par-5 17th and holed a 20-footer for birdie on the par-4 18th.
"I know how Bill feels," Wood said "We all go through that."
Wood also rallied to win the Dick's Sporting Goods Open last month in New York, making a long birdie putt on the final hole of regulation and beating Michael Allen with a par on the first hole of a playoff. That was his first victory since he won the 1996 Deposit Guaranty Golf Classic for his lone PGA Tour title.
"This week feels a little different than the one in New York because I'd won and there wasn't nearly the pressure. I felt much more comfortable and it just fell into place."
Glasson, winless in 47 starts on the 50-and-over tour, shot a 72. He began the round with a four-stroke lead and increased his advantage to five, but gave it away on the back nine. The seven-time PGA Tour winner had five bogeys and three birdies on the final eight holes.
"The last six or seven holes were a roller coaster," Glasson said. "It got a little but iffy between clubs out there, but you have to give Woody credit."
Needing a birdie to win or a par to force a playoff, Glasson hit a sand wedge approach on the 18th that skidded down a bank between the green and a pond. He chipped to 10 feet and missed the putt.
"I hit that putt at 18 too hard. Couldn't get the speed right," Glasson said. "I need to work on some things. If I start missing greens, my short game isn't good enough."
Australia's Peter Senior birdied the final four holes for a 69 to finish third at 12 under.
Tied with Allen, Fred Couples and Roger Chapman for the tour victory lead, Wood earned $270,000 to jump from 22nd to 14th on the money list with $854,817 in 10 events. The top 30 will qualify for the season-ending Charles Schwab Cup Championship in Scottsdale, Ariz.
"I wish we had a tournament next week," Wood said. "I'm confident now. It's been so much fun playing well."