PGA Tour commissioner Jay Monahan and LIV Golf chief Yasir Al-Rumayyan will come face-to-face at the Dunhill Links Championship.
The two rival tours remain locked in negotiations over a peace deal for professional golf, although little progress has been made in 16 months since a framework agreement was announced.
However, a number of key figures will descend on Scotland for this week’s DP World Tour event, where 14 LIV Golf players will compete alongside PGA Tour stars.
St Andrews, Carnoustie and Kingsbarn play host to the unique event – as players rotate around the three iconic courses and compete in two simultaneous tournaments.
Paired up with famous amateurs, the pros score their own ball for the individual competition, while also competing in a team event with their playing partner.
The draw was revealed on Tuesday – and one fourball caught everybody’s attention.
PGA Tour star Billy Horschel will play alongside Monahan in the same group as LIV Golf player Dean Burmester and Al-Rumayyan.
Fans on social media have dubbed it ‘the most awkward round in golf’ due to the ongoing animosity between the PGA Tour and LIV Golf, although that could all be about to change if a deal gets done.
Rory McIlroy tees off moments later alongside his dad, Gerry, in a group with LIV Golf player Louis Oosthuizen and South African businessman Johann Rupert, who oversees the Dunhill Links and has long been pushing for an agreement between LIV Golf and the PGA Tour.
Perhaps more interestingly, McIlroy will play alongside Al-Rumayyan, the governor of the Saudi Public Investment Fund, on Friday, as the groups rotate.
McIlroy, once LIV Golf’s biggest critic, has softened his stance in recent months and pushed for a peace deal to bring golf’s best players back together.
Speaking earlier this year, the Northern Irishman said: “I was maybe a little judgmental of the guys who went to LIV Golf at the start.
“It was a bit of a mistake on my part because I now realise that not everyone is in my position or in Tiger Woods’s position.
“I can’t judge people for making that decision, so if I regret anything, it was probably being too judgmental at the start.
“I wouldn’t say I’ve lost the fight against LIV, but I’ve just accepted the fact that this is part of our sport now.
“We’re professional golfers and we play to make a living and make money, so I understand it.”
McIlroy, who is part of a PGA Tour sub-committee alongside Woods, has grown frustrated with the lack of progress made over a deal.
He is already acquainted with Al-Rumayyan and recently warned that the Saudis could soon grow impatient and start looking at alternative options.
Meanwhile, Monahan failed to provide any concrete update on negotiations with the PIF when he spoke to the media in August.
“It’s stronger,” Monahan said. “That’s a direct result of dialogue and conversation and really starting to talk about the future, future product vision and where we can take our sport.
“I think when you get into productive conversations, that enhances the likelihood of positive outcomes, and that enhances the spirit of those very conversations. I think that’s where things stand.”