Andrew Svoboda parred the first playoff hole on Sunday to top Will MacKenzie and win the Chiquita Classic.
Svoboda carded a 2-under 70 during his final round at River Run Country Club to finish the tournament at 12-under-par 276.
MacKenzie capped a 5-under 67 with a chip-in eagle at the 18th hole to meet him there.
John Peterson, who held a share of the third-round lead with Svoboda, could only manage a 1-under 71 to finish in a tie for third at 11-under. He was joined there by Ben Martin (68).
Ryo Ishikawa (66) owned sole possession of fifth place at 10-under, while Ricky Barnes (70) and Troy Matteson (72) shared sixth at 9-under 279.
Svoboda and MacKenzie went to the first hole for the playoff, where MacKenzie hit his tee shot into the rough to the left, while Svoboda split the fairway.
After MacKenzie sailed his third shot over the green, Svoboda's third settled safely on the green about 30 feet from the hole.
MacKenzie then almost repeated his chip-in at the 18th, but the ball had too much speed and bounced off the flagstick, rolling about 10 feet away.
Svoboda nearly sealed the win with his lengthy birdie effort, but the putt stopped a half a rotation short and he tapped in for par.
Needing to convert his par putt to force a second playoff hole, MacKenzie pushed his effort just wide right to hand Svoboda his second career victory on the Web.com Tour.
"I'm set now for next year," said Svoboda, who finished 25th on the Web.com Tour's regular season money list to receive his PGA Tour card for next season. "I think if I drive it good and my short game is good I will have a chance next year on (the PGA Tour)."
Earlier, Svoboda quickly pulled ahead for the outright lead with back-to-back birdies at the first and second, but then bogeyed the third to fall back to 11-under and a stroke ahead of Peterson, who traded a birdie at the second with a bogey at the third to stay at minus-10.
Following Peterson's bogey at the sixth that dropped him two strokes off the pace, Svoboda birdied the eighth and 10th to move to 13-under and three shots ahead of the field.
MacKenzie, meanwhile, countered a bogey at the third with birdies at the second, sixth, ninth and 14th to sit among a group of players tied for second at 10-under before his chip-in birdie from just off the green at the 18th gave him the clubhouse lead at 12-under.
Svoboda then bogeyed the 17th to fall into a tie with MacKenzie, and could only manage a par at the last to force the playoff.
NOTES: Svoboda collected $180,000 with the win, which moved him into a tie with Trevor Immelman for the top spot of the Web.com Tour finals money list ... Svoboda only made five cuts in 18 starts on the PGA Tour this year ... It was the fifth playoff on the Web.com Tour this year ... Svoboda is the 11th third-round leader/co-leader to go on to win this year ... The tour moves to Ohio next week for the third event of the Finals series, The Nationwide Children's Hospital Championship.