The pair will fight it out over the course of 18 holes for a $9 million prize pot, meaning there will be a serious edge to the event after some light-hearted buildup. Despite the fortunes both men have made throughout their golfing career, there's a serious amount of capital on the line.
Here is a look at how the bookmakers are viewing this one-off meeting between the two legends and a preview of how Capital One's The Match will play out.
To win outright
Woods -1.5 (87-100)
Woods +1.5 (33-100)
Mickelson -1.5 (12-5)
Mickelson +1.5 (87-100)
Odds courtesy of OddsShark
Woods, Mickelson Set for Unique Golfing Spectacle
As Stephen Hennessey of Golf Digest relayed, the course the event will take place at is a bespoke venue:
The preparations for the matchplay duel have seen both men seemingly enjoy themselves, mixing in talk of bets on the opening hole worth $200,000 with semi-serious staredowns. But the competitive gene in both will surely come to the fore when they step on to the opening tee on Friday.
That type of mindset has been crucial not only to these men reaching the summit of the sport, but staying there for as long as they have.
Woods is 42 years old and Mickelson is 48, yet they remain two of the biggest names in golf and still command some of the largest followings at events around the world.
Here are some reminders of why these two players are so revered:
Given their legacies in the game, expect plenty to tune in and for the players to rise to the occasion.
In terms of recent form, there's not a whole lot for punters to go off when picking their winner. Woods was last in competitive action at the Ryder Cup, while Mickelson, another member of Team USA at Le Golf National in Paris, played at the Safeway Open in early October, where he tied 17th.
Woods' last individual outing was at the Tour Championship, where he put together a memorable four days of play to finish top of the leaderboard. After a turbulent few years for the 14-time major champion, this was his victory since 2013.
ESPN Stats & Info summed up just how long he'd been stuck on 79 career titles for:
Perhaps unsurprisingly, after the mental and physical strain of that victory, Woods was not at his best at the Ryder Cup, as he failed to earn a single point for the team. Mickelson also failed to register a win, as the United States were beaten 17.5-10.5 by the Europeans.
The hope for organisers of Capital One's The Match is that both men have had time to rest up ahead of the event and the fresh format brings something extra from the veteran players.
Woods is a worthy narrow favourite, as he's showcased greater form throughout 2018 and is a character you sense will be more zoned in on the day itself. Still, the unorthodox and Mickelson have never strayed too far from one another, and the left-hander will adapt to this occasion better than his longstanding rival.
Prediction: Mickelson to win, 1up