On Friday, Tiger Woods and Phil Mickelson take the course for Capital One's The Match, which can be streamed on B/R Live. The contest will mark the first time the two all-time greats will face off one-on-one. For decades, they've zigged and zagged near each other (and been teammates on Ryder Cup teams). Mickelson went pro first, but Woods won a major first; when Woods struggled in the mid-to-late 2000s, Mickelson rose again. Now, as Mickelson has waned, Tiger has returned to his old, fist-pumping self.

Indeed, they have gone back and forth for nearly two decades, but one-on-one will be a different game, even psychologically. Trash talk will be critical. "It's on," Woods tweeted in August, to which Mickelson replied, "I bet you think this is the easiest $9M you will ever make."

"Phil loves this type of scenario," says Notah Begay III, who attended Stanford with Woods and competed against Mickelson in college. "It's playing into his hand. The gambling aspects, the showmanship—I think it's a wonderful stage for Phil."

Those who knew the golfers early in their careers, from childhood through college, know just how far back the competition between Woods and Mickelson goes. It began three decades ago, in the mid-'80s, as they each established their reputations—Mickelson as a high-schooler, Woods just an elementary school student.

"There was talk that this kid Tiger Woods was winning his age group by 10 to 15 shots," Begay says. "He was better than the rest. He's always played up. From nine years old, when he played against his age group, he'd win three-day events by 20 shots."

By age 12, Woods had established himself as a sort of prodigy and made an appearance in Sports Illustrated's "Faces in the Crowd" section. Wally Goodwin, the golf coach at Stanford University, took note.

"I knew a little about him, and I wrote him a letter," says Goodwin, who is now retired. Goodwin says it wasn't exactly a recruitment letter—Woods was a middle-schooler then—but it was certainly the beginning of a yearslong courting process. "I said, you know, you're a good-looking guy, you got a great smile. If you're interested in college, drop me a note. He wrote me a note, and it became a famous note."

In Woods' reply, he wrote, "I've heard a lot about your golf course, and I would like to play it with my dad some time in the future."

Meanwhile, in San Diego, Mickelson was establishing himself as a prodigy, too.

"From the time he was 15, he was dominating the older age groups across the country," Begay says. "He was sort of a legend already at 15 or 16." At 17, he faced Begay in Palm Springs, California. "I couldn't believe how good he was," Begay says. "He hit it far, hit it high, this big tall left-hander. I was like, Wow, if that's the guy I have to beat, I'm not sure I can do this for a living. It left me scratching my head."

By graduation, Mickelson was one of the hottest golf recruits in the United States. According to the 2010 book, The Last Putt, which covered the '90s collegiate golf scene, Mickelson considered attending Stanford. But on his campus tour, he told Coach Goodwin: "I love it here, Wally. But I don't know that I want to study that hard while I'm playing golf."

Mickelson enrolled at Arizona State in 1988. He was the individual champion at the NCAA tournament in 1989 and repeated in 1990, when his team won it all, too. In 1991, during Mickelson's junior year, Begay and Casey Martin debuted as freshmen at Stanford.

"Phil had a massive presence at that age," says Martin, who is now the head golf coach at the University of Oregon. "He was certainly known for his short-game heroics. He was so far advanced in the short game from other college players it was sort of embarrassing. He was a true legend."

By the 1992 season, which Mickelson dominated again, rumors swirled at Stanford that Woods might someday become a Cardinal. Begay and Martin, who were both economics majors falling behind on schoolwork, decided to redshirt their junior seasons so that their senior years could coincide with Woods' freshman season. In 1994, Woods arrived.

It was, Martin says, "Like Michael Jordan coming in, or LeBron. You know you're looking at absolute greatness. Here Phil was, senior year, and he'd already won on tour—that doesn't happen—and everyone would conceive Tiger was better than Phil! It was intimidating and fun to be around."

Still, in some ways Woods was a normal student. "He had typical freshman duties," Goodwin says. "Get the luggage into the van when we got someplace; then get it out of the van and take it to the front desk. Then he won his first tournament, so that ended that requirement."

In 1995, Woods won the U.S. Amateur, but his Stanford Cardinal would lose the NCAA tournament by a single stroke. The following year, Woods made a significant leap.

"That year, we won half the tournaments we played in," says Joel Kribel, a teammate who arrived to Stanford one year after Woods. At the Pac-10 championship, Woods shot a 61—11 strokes under par—and broke the course record. Then, at the '96 NCAA tournament, Woods won the individual title. (His Cardinal fared a little worse, placing fourth.) Around that time, Kribel says, "I realized, it's not like he's just better than everybody—he was leaps and bounds better than everyone in college."

He continues: "I didn't think anyone could get as good at golf as he did. He made the rest of the guys out there, and I was one, look pretty average, when they were really good players. He made people who'd been No. 1 look like they didn't stand a chance. If he was playing halfway decent, it was kind of soul-crushing for a lot of guys to know, I could play my best and get lapped by this guy."

As Woods' collegiate career took off, he became a celebrity. "Whenever Tiger's around, it's crazy," Begay says. "It's a hundred times the interest. Our home tournament at the Stanford Golf Course, we had 2,500 people out there for a college tournament, and I think they had 100 requests for media credentials. And as soon as Woods graduated, it went back to one or two media requests and 20 people following."

Woods would go on to win 14 majors, second all time, including three in 2000 alone.

Mickelson has five major victories to his name, with the most recent among them the 2013 Open Championship.

Perhaps there's no debate as to who the better golfer has been over the decades, but Friday we will find out who is superior when it's one-on-one, at age 40-something.

"It'll be fun to watch," says Martin, who's seen both players up close for years. "Anything can happen in 18 holes."