Novak Djokovic is on the cusp of what would be the crowning achievement of the Golden Era in men’s tennis: the Calendar Grand Slam. He’s won his first 27 matches in majors this year, bagging titles in Melbourne, Paris (after beating perennial gatekeeper and historic rival Rafael Nadal in the semifinals), and London. After a pretty arduous route to the final of the U.S. Open, Djokovic is one match away from yet more record-breaking in a career that is already crammed to the brim with records.

Daniil Medvedev, world number two behind Djokovic, will be his opponent. Medvedev is a great hard court player, having made the 2019 U.S. Open final and the 2021 Australian Open final, with a handful of Masters 1000 titles as well. Yet he’s also come up with some pretty disappointing performances in big matches, one of which being the aforementioned final in Melbourne this year.

I’ve followed Medvedev’s matches pretty closely since his breakout run and spectacular final performance at the 2019 U.S. Open. I wrote at length about him late last year. Sometimes, I like his game so much that it leads to me overrating him significantly. I even thought he would beat Djokovic in the Australian Open final — this was a second-time major finalist up against an eight-time champion of the event. Suffice it to say that I am not making a similar prediction tomorrow.

I’ve thought about the Australian Open final a lot this year. I’ve rewatched it in its entirety and been through the highlights several times. And it’s still a mystery to me. You can look at the scoreline — 7-5, 6-2, 6-2 for Djokovic — and see the pretty straightforward drubbing that it was. Those numbers aren’t hiding any deep secrets. But it was a bizarre match for a variety of reasons.

One might think that after cruising through six rounds of pretty comfortable opposition, Medvedev was simply rocked by the typically vicious level of play Djokovic brings to Australian Open title matches. But after predictably falling behind 3-0 in the first set, the Russian played several great games, breaking back and serving up a few easy holds. At 5-6, Djokovic pulled a wonderful return game out of the hat, and that was that for the first set, but I wasn’t then worried for Medvedev. I thought he’d settled in nicely and was matching Djokovic’s pace, just fell to a burst of brilliance from the king Down Under.

At first, this impression seemed like a decent one. Medvedev broke Djokovic to open the second set, then at 1-0, 15-all, defended a backhand down the line and a drop shot, finishing the point with a no-pace overhead smash that fooled Djokovic.

And then he lost the plot.

Djokovic would win three straight points to break back — Medvedev would miss two of three first serves, but Djokovic forced errors on all three points. Fine. Disappointing to lose the break, I’m sure, but patches of play like that from the great Serb are to be expected. But then, with Medvedev up 15-30 in the next game, the Russian hit three consecutive unforced errors, two of them from winning positions in rallies. At 1-2, Medvedev was broken again. Every point he lost in the game was due to an unforced error.

From a set and a break down, Medvedev’s level didn’t rise much. At 2-4 down in the third set, he finally played a good return game, blasting two winners for 15-30 — but at that point Djokovic had entered wall mode and held serve anyway with an array of stunning tennis that had him celebrating feverishly. The final was over one game later.

As great as Djokovic was for virtually all of the match, it wasn’t as if he had played in the same holy vein as his 2019 final performance in Melbourne. I couldn’t stop thinking about why Medvedev had been so lackluster — this was a guy who had beaten Djokovic three times, including a sound win in their most recent meeting. At the ATP Cup in 2020, he had fallen 1-6, 7-5, 4-6 to Djokovic, but had been virtually perfect for the last two sets, helping make the match a true physical grind.

This was one of the reasons I’d been so big on Medvedev — he actually seemed occasionally capable of beating the Serb at his own sliding, contorting game of attrition from the baseline. He had a big serve and a return to match. I would watch points like the second one in this compilation —

Djokovic vs Medvedev matches are on a different PLANET. @DjokerNole @DaniilMedwed #USOpen pic.twitter.com/4N9eVeJRDW

— Tennis TV (@TennisTV) September 11, 2021

— and think that Medvedev had it in him to dethrone the Serb at a hard court major (Medvedev plays a lot of points like that. He doesn’t win them all, but almost always recovers faster than his opponents, making runs as he breaks them physically). But now my feelings have changed slightly, and not just because Djokovic is showing no signs of slowing.

Medvedev’s runs to major finals — while impressive — haven’t really stunned because of the level of his opposition. He tends to absolutely roll over opponents who can’t hit through him. In his first set against Pablo Andújar this tournament, he lost just five points. But matches against much better opponents are more instructive.

At the 2020 U.S. Open, Medvedev lost in the semifinals to Dominic Thiem 2-6, 6-7 (7), 6-7 (5). It was a high-quality, competitive match, but the Russian failed to extend it to even a fourth despite serving for the second and third sets and having set point in each. He then lost a remarkably similar match to Stefanos Tsitsipas at Roland-Garros this year. Much of the match was glorious nip and tuck, but after a poor first set, Medvedev was consistently second best in the tight moments. Despite having set points in frame two and being up a break in the third, each set went unclaimed.

Like with the Australian Open final, Medvedev had a stretch where he simply lost concentration, and his game with it. In each of the two above matches, it was the first set, putting him at instant disadvantages. And against Djokovic, it was the middle of the second through the middle of the third, sinking his deficit from large to inescapable. This, more than any flaw in Medvedev’s game, is what makes me wary to say he’ll push Djokovic to the brink tomorrow. The possibility is there and it is tangible that Medvedev will go badly off the boil, leaving his top-class opponent to run away with a few games.

The tireless, give-nothing-away Daniil Medvedev of the ATP Cup and World Tour finals last year can give Djokovic hell. But I’m not sure we’ve seen that version since the latter tournament; opponents significantly worse than he is aren’t a good barometer for that mode being present.

Take Medvedev’s semifinal with Félix Auger-Aliassime. The first set was a Medvedev serving clinic. Not at all instructive for the final; Djokovic returns far more effectively than the Canadian and serving levels are often fickle. The second set saw Medvedev escape narrowly as his younger opponent collapsed from a winning position. This is more relevant information — Djokovic won’t be so giving in the final, so Medvedev will need to play significantly better. He then won the third easily as Auger-Aliassime’s resistance faded.

Medvedev tends to win matches like these without blinking an eye. He’ll make balls relentlessly and return deep, forcing you to bash harder and harder to hit winners. When his opponents are wasted, he can become untouchable on serve, slamming rockets past their spent souls. But when faced with stern resistance, when his usual tricks (which work on the vast majority of his adversaries) aren’t enough to get the job done, there often just isn’t a working plan B in place.

This is something I wrote after Tsitsipas beat Medvedev at Roland-Garros and that I’ve been thinking about a lot. I think Medvedev can win tomorrow — he’s fresher and has the tools — but he needs to be so, so good right from the start, like the last two sets of the ATP Cup match. pic.twitter.com/JgojJgCR6g

— Owen (@tennisnation) September 11, 2021

Sometimes there is. Sometimes it’s even stellar, like when Medvedev dug his heels in against Nadal at the U.S. Open and when he started net-rushing against Thiem at the World Tour Finals. But Medvedev’s developed a weird reputation as a strategic genius (admittedly, I’ve bought into this narrative too), when in reality his exhibits of tactical mobility are isolated rather than a concrete pattern.

Again, Medvedev can give Djokovic hell. But based on his last few best-of-five matches against top-tier opponents, there’s not a lot of reason to believe that he will. It’s certainly a possibility, but not one I’m remotely willing to (metaphorically) bet on any longer.

In contrast, and despite the pressure of the occasion that’s sure to fall more on the shoulders of Djokovic, evidence that Djokovic can and will bring the full weight of his game crashing down on Medvedev is abundant.