So it only seems apropos that the two would cross paths again as the former world No. 1 appears poised to launch a new chapter in his storied career.
The first time was at the 1996 Las Vegas Invitational, when Woods outdueled Love in a playoff for his first victory on the PGA Tour.
Seventy-eight Tour victories, 14 major titles, three swing changes and multiple injuries and ailments later, the two seem to be on a collision course at a hot and humid Sedgefield Country Club.
Woods ignited a record crowd with a second-round 65 at the Wyndham Championship to take a share of the lead alongside little-known rookie Tom Hoge, while a resurgent Love was just a shot back after a 66 on Friday.
It’s something of a throwback title chase that both veterans have embraced, although for vastly different reasons.
“These last couple of days have been nice. I’ve put the ball in the right spot but also I’ve got a few nice bounces and lies here and there and it’s very close,” said Woods, who moved into the lead at a Tour event for the first time since the 2013 WGC-Bridgestone Invitational. “You don’t realize how close it is from switching.”
Although Woods ventured to the Piedmont Triad because of his position on the FedEx Cup points list - he’s currently 187th and needs to win or possibly finish alone in second place to advance to the playoffs - it was likely Love who persuaded him to play the Wyndham Championship for the first time.
The two played multiple practice rounds together last week at the PGA Championship and again late Tuesday afternoon when they arrived at Sedgefield.
It’s become an expanding relationship born from necessity.
Late last year, in the aftermath of the U.S. Ryder Cup team’s loss at Gleneagles, Love and Woods were named to the Ryder Cup task force, and their friendship has grown from there one text message at a time.
“This whole task force, all of us, I’ve spent more time talking to Phil Mickelson and Tiger Woods this year than I ever have,” Love said. “We asked, 'What is wrong with the Ryder Cup?' What we realized is that the guys didn’t talk. We’re all getting to know each other better.”
For Love, the practice round with Woods on Tuesday inspired the 51-year-old to stop worrying about making cuts and start focusing on winning tournaments again. As for Woods, well, he doesn’t seem to need much inspiration at this point.
After opening with his lowest Tour round in two years, a 64 on Thursday, Woods played a scrappy opening nine before turning back the clock on the inward loop, making back-to-back birdies at Nos. 12 and 13 and producing a familiar roar when he rolled in a 10-footer for eagle at the par-5 15th to grab a share of the lead.
Although Woods was in a similar playoff position in 2011, when he was 129th in points, he chose not to play the Wyndham Championship. With much longer odds this time, it’s not a stretch to consider Love’s influence on Woods decision to play the North Carolina event and give his season, not to mention his swing, one final chance.
In what could best be described as a symbiotic relationship, Love was inspired by Woods’ unwavering competitive outlook, while Woods may have discovered that classic doesn’t necessarily mean confining when it comes to golf courses.
“I learned a lot playing with Davis,” Woods said. “This golf course is speeding up. That’s where the practice round with Davis helped, because of some of the irons he told me he hits off tees. It definitely helped playing with him.”
If he continues to play the way he did on Friday, when he hit 8 of 14 fairways and 15 of 18 greens in regulation, he may also credit next year’s Ryder Cup captain an assist late Sunday afternoon.
Just imagine what could have been if Woods hadn’t avoided the cozy confines of Sedgefield – or Harbour Town and Colonial, for that matter – for the better part of his Hall of Fame career?
The way he’s picked apart this classic Donald Ross design, Woods might not be chasing Sam Snead for the all-time Tour victories mark. He might be ahead of him.
In another twist of fate, Snead won his 80th Tour title in Greensboro 55 years ago. Woods, who trails Slammin’ Sammy by three titles, would win his 80th Tour event this week if he can hold off the likes of Hoge.
Following his round, Woods was asked if he knew anything about Hoge, a rookie who, as fate would once again have it, has played 79 Tour rounds?
“No, what is it, or him?” Woods replied.
In Woods’ defense, he was probably more interested in Love’s fortunes and a possible sequel to that Vegas bout 19 years ago, a precursor of what was to come and what could be again on Sunday at Sedgefield.