'Playing Hale in a playoff isn't the first guy you want to choose,' said Green, who matched 68s with Irwin in the final round to finish regulation tied at 14-under 199.
But the truth is Irwin, the 50-and-over circuit's all-time win leader with 34 career titles, came into the week winless in four tries in playoffs. Although he was able to exchange pars with Green over the first six holes of sudden death, Irwin missed the green at playoff hole No. 7 then failed to hole his chip to extend the extra session.
'I don't mind playoffs, I'm just not having much success in them,' said Irwin, whose overtime record dropped to 0-5.
The Long Island Classic was the third straight event to end in a playoff - a first on the Senior Tour. Bob Gilder won last week's FleetBoston Classic by beating John Mahaffey on the third extra hole. The week before, Gilder got the better of Irwin in a one-hole playoff at the SBC Senior Open.
Irwin, who averaged over 30 putts per round this week, missed a 15-foot birdie to win on the first playoff hole - the 167-yard, par-three 18th - a hole he and Green would play four times on Sunday.
Both players made mediocre approaches en route to pars at the 12th and 13th, the second and third extra holes. Green had a good chance to end things on the fourth - back at 18 - but pushed his seven-foot birdie attempt right of the hole.
Irwin seemed to have the advantage at the fifth hole of sudden death when Green's shot to the 12th green rolled into a bunker. Green, faced with a long shot from the sand, blasted out to three feet and saved par. Irwin then grazed the right edge of the cup with his birdie effort from 18 feet.
After they traded their sixth straight pars of the playoff on the 13th, Irwin and Green headed back to the 18th tee. While Green's tee shot landed on the back of the green, 25 feet from the hole, Irwin's ball flew left toward a bunker but got caught up in a nice lie just off the putting surface.
Irwin's lucky break was negated when Green carefully rolled his long birdie putt into the heart of the hole. Irwin managed a smile then tipped his cap toward his competitor, and a moment later lost when he missed his chip.
'Hubert played very well today,' said Irwin, who has seven top-two finishes this year, including a pair of victories. 'He hit a lot of good shots and kept his composure.'
Green collected $255,000 for his first win since the 2000 Kroger Senior Classic.
Irwin compiled a 4-5 playoff record while on the PGA Tour. His last overtime win was a big one; he beat Mike Donald on the 19th hole of a scheduled 18-hole playoff to win his third U.S. Open title at Medinah in 1990.
Green, who won the 1977 U.S. Open and the 1985 PGA Championship during his 19-win PGA Tour career, trailed Irwin by two shots with three holes to play in regulation Sunday.
At the 16th, Irwin hit his approach to five feet but missed the subsequent birdie try. Then Green, who stuffed his shot to half the distance on the same hole, sank his short birdie to trim the margin to a single stroke.
Irwin made only his second bogey of the week after he found a greenside bunker with his third shot to the par-5 17th. He couldn't convert the up-and-down out of the sand and dropped into a tie for the lead with Green at 14-under.
'That was a mental lapse. I just didn't hit it hard enough,' Irwin said of third at 17. 'It just wasn't meant to be today.'
Allen Doyle, a runner-up here in 1999 and 2001, turned in a 5-under 66 - the co-low round of the day at the par-71 Meadow Brook Club. He tied for third at 11-under with Morris Hatalsky (70), who began Sunday's round one shot back of co-leaders Green and Irwin.
Bruce Fleisher, the Long Island Classic champion in 1999 and 2000, closed with a 70 for solo fifth at 10-under 203.
Bobby Wadkins, who became the youngest player to win on the Senior Tour when he captured last year's title at the age of 50 years and 10 days, tied for 15th at minus-six.