2017 AO: Dimitrov vs Wawrinka -- Hmmm... This is a tough one. I feel like I want to give Grigor the edge based on the way they were playing, the fact he won their prior match, but a slam final is a whole other thing, and I give Stan the mental edge. If he pushes Roger close in a match that's usually a sign he's playing pretty well
2017 RG: Thiem vs Wawrinka -- Thiem will choke. Stan, easily.
2017 WI: Berdych vs Cilic -- Berdych's run here, like basically the entire bottom half of the draw, is a joke. He is completely washed by this point, and no way he's beating the Cilic who beat Querrey and Muller, but if Cilic is still going to have the blister issue he had in the final? Berdych wins.
2017 US: Anderson vs Del Potro -- Del Potro, obviously. He was exhausted by about halfway through the Nadal match, but if he's fit enough to win that one then he'd definitely win this one.
2018 AO: Cilic vs Berdych -- Cilic, easily. Not even close. Why is this even an interesting hypothetical? He wasn't as good as he was at Wimbledon `17, but he was still a lot better than Berdych was by this point.
2018 RG: Thiem vs Del Potro -- This is closer than the Thiem-Wawrinka one the year before just because Del Potro is not as good as Stan on the surface, but I still think he's good enough to beat this absolute mental midget.
2018 WI: Del Potro vs Anderson -- IS THIS REALLY A QUESTION?!
2018 US: Thiem vs Del Potro (semifinals) -- Wow, this is an interesting one... Thiem is a much better player by this point than he was when they met here in 2017, but I'm still going with Del Potro. Easily.
2019 AO: Medvedev vs Stefanos -- This is interesting because Medvedev is not yet the player he would turn into at Cincinnati later this year, and this was Stef's step into the big time, but Daniil was playing well, and he still, even then, completely owned Tsitsipas. That he beat Stef fairly comfortably in New York in 2018 after the dude had been to the final in Canada was pretty telling.
2019 RG: Thiem vs Wawrinka -- Wawrinka is finished by this point. Not sure where he came up with that performance against Tsitsipas from, but no way is he beating this Thiem.
2019 WI: Querrey vs Bautista-Agut or Nishikori vs Bautista-Agut -- This was sort of Querrey's last hurrah, and he was playing some seriously nice stuff that Wimbledon, but I'm not sure I see him getting past Roberto, who was on it. Same for Nishikori.
2019 US: Medvedev vs Berrettini -- Medvedev.
2020 AO: Thiem vs Raonic -- Raonic had a couple of really good performances here, but no way is he beating Thiem. The guy took Djokovic five. Forget about it.
2020 RG: Stefanos vs DieGOAT -- Stef has the higher ceiling, but the conditions favour Diego. Might give the edge to Tsitsipas, but I could go either way. It'd be close. I could see Stef being a heavy favourite and choking under expectation.
2021 AO: Medvedev vs Zverev -- Medvedev.
2021 RG: Stefanos vs Berrettini -- Normally I would say it's got to easily be Tsitsipas, but given the circumstances under which he played that final I'm not sure he's beating any player playing well, no matter what kind of start he had... Still, probably go with Stef
I think Berrettini getting a walkover in the 4th round massively flatters his run there that year.
2021 WI: Berrettini vs Shapovalov -- Berrettini.
2021 US: Medvedev vs Zverev -- Medvedev, though Zverev really was pretty good here.
2022 AO: Medvedev vs Berretinni/Shapovalov -- Given Medvedev apparently had a hernia I might give Berrettini the edge against him, but... I mean, if he was good enough to get out to a 2 set lead against Nadal, I'm not sure I see Berrettini coming back from that against him.
2022 RG: Zverev vs Ruud or FAA vs Ruud -- Zverev would destroy Ruud. Felix is more of a hypothetical, but I feel like he could out last him too.
2022 WI: Sinner vs Kyrgios -- Interesting. I think Sinner has the game to absolutely rattle Kyrgios, and looking at the way he was playing against Alcaraz and Djokovic I think he would, but... I also look at the way he folded in a QF up 2 sets to nothing, and I think the same thing could easily happen if he was playing in the actual final. The question is would Kyrgios be good/cool-headed enough to come back in that situation? That I'm not sure about. Edge to Sinner.
