Both of them know the pain of coming close to winning their first major. By keeping it straight and simple at Sahalee Country Club, both of them got into contention once again Friday.
Singh made five birdies on the first nine holes and matched the course record that Tiger Woods set the day before, a 4-under-par 66 that put him at 136 going into the weekend.
"Each year you play, you gain a little more experience, a lot more know-how to handle a situation like I'm in now," said Singh, who came up two strokes short of a playoff in the 1993 PGA Championship.
Right behind him was Montgomerie, in pursuit of his first major championship and in contention for the first time since he lost by one stroke to Ernie Els in the U.S. Open last year.
He made three key par saves in a round of 67 that put him at 137, along with Scott Gump and Steve Stricker.
"I haven't come over here to finish second," said Montgomerie, who has done just that in three previous majors. "The hardest thing to do is get into contention. We'll go from there."
The high, heavenly ground of Sahalee was full of high hopes for a couple of players chasing history.
Davis Love III is trying to become the only repeat winner since the PGA went to stroke play in 1958 and the first since Denny Shute in 1937. He worked his way into the hunt with a 2-under 68.
That left him just two strokes back at 138, along with Woods, Brad Faxon, Andrew Magee and former PGA champion Steve Elkington.
And never count out Mark O'Meara, undaunted by the pressure of trying to become the first player since Ben Hogan in 1953 to win three majors in one season.
Just like he did in winning the Masters and the British Open, the 41-year-old O'Meara just plugged along until making a thrilling move that thrust him to 3-under, one off the lead.
O'Meara threaded the "goal post" trees guarding the par-5 11th green with a 3-iron, then holed a 15-footer from just on the fringe for eagle that drew him within one stroke of the lead.
He dropped back with bogeys at the 12th and 15th holes and finished with a 70 for 139, just three strokes back but in good shape for the weekend. O'Meara was five back midway through the Masters, and three back after two rounds at Royal Birkdale.
"He is unflappable," said Love, paired with O'Meara the first two days. "The crowd was yelling to him, `Make it three!' He wouldn't let the crowd bother him."
Woods couldn't hold a first-round lead for the second straight major. He followed a 65 in the British Open with a 73. And one day after making seven birdies at Sahalee, he didn't get his first until the 16th.
"I made a lot of putts just to hang in there," Woods said. "I'm only two back, and that's perfect. That's where I need to be."
Stricker became only the fourth player to reach 5-under at Sahalee, but it didn't last long. After four birdies on the first seven holes on the back nine gave him the lead, he took double bogey at No. 17 when he hit 5-iron into the water.
"It was an up-and-down day, but the course will do that," Stricker said.
Indeed, a tight, tree-lined Sahalee made for a wide-open weekend -- 13 players are within three shots of Singh. Only three of the 20 players who broke par in the first round managed to shoot in the 60s on Friday -- Stricker, Gump and Elkington.
And of the the 14 players under par, only David Frost managed to play the back without a bogey.
"The key to winning a major is you need to peak at the right time," Singh said. "I played well last week and I'm playing well again. All I need to do is go out there and do what I did today."
As Woods proved Friday, that's not always easy.
He left the driver in his bag once again, but that wasn't the problem. Woods missed a 5-foot birdie putt on the second hole, three-putted on No. 4 and took another bogey after hitting his 3-wood into the rough on the 480-yard, par-4 sixth.
He had a three-putt bogey on No. 15 from 25 feet. Woods took 34 putts on Friday, after needing 27 the day before.
Singh, who has won five times on the PGA Tour and 18 other times around the world, was a relative unknown in the PGA in 1993 when he finished out of the playoff at Inverness, which Paul Azinger won over Greg Norman.
The one area he has scaled back on is the long hours that he puts in on the driving range.
"If you know what you're doing and if you're hitting the ball well, you don't need to spend that much time on the range," he said. "But you can never practice enough putting."
Singh's only lapses were missing the green on the par-5 11th with a 9-iron and hitting into the bunker on the par-3 17th, the only two bogeys in an otherwise steady performance.
Montgomerie took a different route, holding his round together with superb par saves on three consecutive holes on the front -- from the edge of the cart path on No. 6, from the bunker on No. 7 and with a 30-foot putt on No. 8 after missing the green to the right.
"There's always a key hole in the round that keeps the momentum rolling along, and No. 6 was the hole," Montgomerie said.
The group at 139 included O'Meara, Frost, Frank Lickliter, John Cook and Glen Day. No one else was under par.
Phil Mickelson took a double bogey on the par-5 second hole but still managed a 70 and was at even-par 140. Paul Azinger needed a birdie-birdie finish to salvage a 73 and was at 141, along with Fred Funk and Scott Hoch.
"I'm due for some good luck, and some good golf," said Elkington, who beat Montgomerie in a playoff in the 1995 PGA at Riviera.
Elkington's picture, along with other past champions, is on a banner hanging from the tented roof in the interview room, which caught Montgomerie's attention.
"You've annoyed me because there's a picture of Steve Elkington up there," the Scotsman said, joking.
But the majors are no laughing matter. At 35, Montgomerie says he has eight competitive years left. And despite leading the European tour money list a record five years in a row, he knows his career will not be complete without a major.
"If I can putt anything like I've been doing the first two days, I'll have an opportunity," Montgomerie said.
Sahalee played a little bit faster than Thursday, when only 20 players broke par.
"It was like Sunday afternoon at a major," Faxon said.
Tom Watson shot 76 and missed the cut at 148. It was the first time in his Hall of Fame career that Watson went through a year without making the cut in a major.
David Duval, the leading money-winner on the PGA Tour, also shot 78 and was headed home early. His worst finish in a major this year was a tie for 11th in the British Open.
Justin Leonard, who had failed to break par just once in 13 previous PGA Championship rounds, followed a triple bogey with a double bogey, shot 77 and missed the cut.
Those who squeezed in include hometown hero Fred Couples at 145, and Ernie Els at 144.
The key to Sahalee is to keep it straight and keep it simple. The explanation for Singh's 66 was the same one given by Woods on Thursday.
"I played a lot to the middle of the greens today, which I thought was the key to my round," Singh said. "If I keep doing that this weekend, I'll have a chance."
The same goes for Montgomerie, and also Faxon. All of them are looking for their first major, and the PGA Championship has proven to be a perfect breeding ground for that -- nine of the last 10 winners were first-time major winners.