Chopra saw a three-shot lead slip away over the last five holes of regulation as Stricker made a run down the stretch, finally catching the Swede with a birdie at the 18th hole.
They finished regulation tied at 18-under 274 and followed each other around during the first three playoff holes, hitting similar shots for the same results: three straight pars.
Stricker hit an errant drive into the rough at the fourth extra hole, the par- four ninth, a costly shot that was followed by Chopra's hybrid onto the green.
After Stricker chipped 15 feet past the hole, Chopra was left tortured by a 23-foot eagle putt that hung impossibly on the edge of the cup. But it didn't matter.
Chopra tapped -- tapped -- in for his birdie, while Stricker missed his mid- range try. The end came more than an hour after Chopra missed by inches on a birdie putt at the 18th hole that would have given him the win in regulation.
He also left a birdie putt on the edge of the cup at the second playoff hole, then missed a 19-footer with the sun in his eyes on the third extra hole.
All the drama ended in Chopra's second career PGA TOUR win -- his second victory in three starts, actually, after going more than 130 starts and nearly four seasons without one.
'All those putts in the playoff and regulation I hit exactly the way I wanted. It just felt like there was a goalie in the hole. I though maybe it wasn't meant to be,' said Chopra, who closed with a 7-under 66 in the final round.
He won $1.1 million and a Mercedes-Benz.
Stricker fired a nine-under 64 on Sunday, tied with Hunter Mahan for the low round of the tournament, and played his last 14 holes in regulation at 9- under par.
The two-time reigning Comeback Player of the Year, Stricker earned his spot in this field by winning last year's Barclays, the first event of the new playoffs.
His tournament this week began with a 38 on the front nine on Thursday.
'I didn't get off to a good start this week and was kind of behind the eight ball. But from then on I played really solid,' said Stricker. 'I just came up a little short.'
Stephen Ames shot a seven-under 66 and finished alone in third place at 17- under 275, one shot out of the playoff. Mike Weir, the leader after the second and third rounds, closed with a 70 Sunday and was another stroke further back at 276.
Mahan (64), Jim Furyk (68) and Nick Watney (71) finished at 278.
The drama for Chopra on Sunday wasn't limited to just the playoff. After beginning the round two shots off Weir's overnight lead, he was ahead by two strokes after making his fourth birdie at the seventh hole.
Stricker pulled even when he holed out for an eagle ahead at the par-four 12th, but Chopra responded with three consecutive birdies from the 11th hole to take a three-shot lead.
Yet Stricker wouldn't go away. He two-putted for a birdie at the par-five 15th to get within a couple shots again, and made another birdie at the 16th to close the gap to one.
He lipped out a birdie putt at the 17th, then turned a poor drive into his closing birdie at the 18th by rolling in a 19-foot putt, tying Chopra for the lead
'I was so impressed by how well he was chasing considering I was making birdies,' Chopra said.
Chopra finished regulation with five consecutive pars. The 15th hole produced a bizarre series when he duffed a chip into a sprinkler hole -- a fortunate break considering the ball would have rolled back down the fairway.
Chopra smashed his longest drive of the tournament at the 18th hole in regulation, sending it 366 yards into prime position on the fairway. But he flew the green with his approach, getting relief from the grandstand.
After a soft chip rolled to 13 feet, Chopra came up about an inch short on his birdie try to force the playoff. It was the first in a series of cruel misses.
Stricker also had a run-in with oddity. At the first playoff hole, the par- five 18th, after he missed the green short with his second shot, Stricker opted to putt the ball from more than 100 feet.
His ball hit Chopra's mark a few yards onto the green, skipping enough to leave his try 10 feet short of the cup. Both players eventually missed birdie putts, but Stricker regretted afterwards not at least asking Chopra to use a smaller mark.
'It was disappointing, but I'm happy with the way I played this week,' Sticker said. 'It's just building blocks for me. I'm going in the right direction.'
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