The win was Delsing's first on the Buy.Com Tour, while the runner-up finish was Freeman's career best.
At the fourth playoff hole, the par-4, 437-yard 18th, Freeman drove deep into the left rough and had no choice but to pitch out into the fairway. Delsing found the right rough off the tee but he played his second on to the green, 20 feet from the hole.
Freeman reached the green with his third but was farther away for par than Delsing was for birdie. Freeman lagged his par save to two feet, but Delsing left himself two feet for the win.
Delsing birdied the last hole on Sunday to force the playoff. Fading daylight caused the players to complete only one sudden-death hole. They returned at 9:00 a.m. (ET) Monday morning to determine the victor.
At the second playoff hole, the first on Monday, both players were inside 10 feet for birdie, but Freeman missed his putt and tapped in for par. Delsing's birdie try also slid by the hole meaning the players would walk back to the 18th tee.
Delsing missed the fairway at the third playoff hole and put his second shot short and right of the green, 80 feet from the cup. He chipped to 10 feet and then watched as Freeman had 35 feet for the win. Freeman's putt missed the hole but tapped-in for par. Delsing followed by holing his 10-footer to extend the playoff.
The duo finished at 17-under-par 263 and they each posted rounds of 5-under 65 on Sunday.
Rick Price finished the tournament in third place, one shot out of the playoff at 16-under par.
Pete Morgan, Pat Bates, Charles Raulerson and Matt Peterson shared fourth at minus-14.
Full-field scores from the Buy.Com Fort Smith Classic