Now he's not even in this year's field.
"I had my shot and I blew it," Perry said at the Honda Classic in early March.
With a two-shot lead with two holes to go in 2009, Perry had one arm in a green jacket. As it turned out, all he needed to do was par one of those holes and make no worse than a bogey on the other.
Of course, he bogeyed both and then lost in a three-man sudden-death playoff to Angel Cabrera.
The other member of that playoff was Chad Campbell. He's not in the Masters this year, either.
The difference between Campbell and Perry is their age. At 36, Campbell will likely qualify for the Masters again.
Perry, who is 50, probably won't.
"I knew it was going to happen and I don't think it's unfair," Perry said "I'm 50 years old, let's be realistic."
Perry's play fell off in 2010 when he had one top-10 finish in 20 starts (a tie for sixth in the season-opening Tournament of Champions). In contrast, he won twice and had eight top-10s in 2009 in 24 starts.
Perry, who has 14 career PGA Tour wins, could still get back to the Masters by winning on the PGA Tour before the 2012 Masters. Right now, the only Champions Tour event he committed to is the Senior PGA Championship. Other than that, he's playing the PGA Tour, where he's played six times without success (three missed cuts, one withdrawal, a tie for 43rd and a tie for 61st).
When interviewed in mid-March, Perry had three tournaments leading into the Masters where a win would get him to Augusta. He missed the cut in the Transitions (74-75), withdrew from the Arnold Palmer Invitational with an injury after a first-round 79 and then didn't play in Houston last week, as he had hoped.
"I'm just playing golf," Perry said. "I don't have the aspirations and drive I had. I did all I could do. I'm very happy with what I did. I'm just enjoying the last couple of years and move on."
This year's Senior PGA Championship is at Valhalla, the site of Perry's 1996 collapse in the PGA Championship. That year, he had a one shot lead going to the 72nd hole, made bogey and lost an 18-hole playoff to Mark Brooks.
Do fans still talk to him about what happened at that PGA Championship?
"Nobody even remembers it," Perry said. "The Masters is still pretty fresh in their mind."
After shooting 12-under-par 276 in the 2009 Masters that got him in the playoff, Perry checked in 13 shots higher last year. His 289 tied for 26th place. He did have three eagles - including two in the third round when he only shot 72.
What happened in the 2009 is ancient history to Perry now.
"When you think about it, you can be depressed or you can forget about it and move on," he said. "And I'm trying to move on. I just had a grandson recently; the heck with golf."
He's even come to terms with the bad break he suffered on the first playoff hole, No. 10. His drive picked up some mud, which made it difficult to control the flight of his second shot. It went left of the green and he couldn't save his par from there. Cabrera hit the green in two shots and two-putted for par to win.
"That was part of it," Perry said of the mud ball. "I got a lot of good breaks, too."
Perry's not sure how he would have played if he was in the Masters this year. Augusta National Golf Club requires a player to hit generally high shots to score well.
"I've just struggled so much with flighting the ball," Perry said. "I hit it so much lower than I used to hit it.
"My driver, I'm hitting it so low and hard," he said. "I can't seem to make the ball stop around the hole."
Perry was paired with Davis Love III in the third round of the Honda Classic.
"He was hitting it so high it was awesome to watch," Perry said. "I told Justin (Perry's son and caddie), 'that's the way I used to hit it.' I don't hit it like that anymore. I can't tell you why. I can't answer that question."