However, this exciting rivalry failed to materialize primarily due to Medvedev's unexpected and unfortunate decline, which was triggered by a painful loss at the hands of Rafael Nadal in the 2022 Australian Open final.
He had come very close to achieving the impressive feat of following up his maiden Grand Slam title by winning the next major tournament. However, the losses he experienced in Melbourne last year pushed him into a dark mental space, and it took him nearly 12 months to fully recover.
Djokovic has unresolved matters in this rivalry, and he will be seeking answers in New York this coming Sunday. His aspiration to achieve a historic calendar grand slam in 2021 was shattered by Medvedev, leaving him heartbroken and in tears after a decisive defeat in the championship match at the US Open.
Earlier this year, he displayed remarkable dominance, raising the possibility of an undefeated season. However, that prospect was abruptly quashed by Medvedev in the semifinals of the ATP Dubai tournament in March.
While Djokovic has delivered exceptional performances on grass following the decline of Roger Federer, it's on the hard court where he has appeared nearly invincible ever since establishing himself as a top-tier player.
In recent years, the only player who consistently posed a significant challenge to him on this surface was Medvedev. This is precisely why the upcoming US Open final matchup between them is not only worthy but could be even more intriguing than another Djokovic-Alcaraz showdown.
Medvedev has reclaimed his rightful place at the pinnacle of men's tennis, consistently outperforming players with higher rankings and contending for major titles on hard courts. He initially earned this status through extraordinary dedication a couple of seasons ago.
However, all his tireless efforts were undermined by the challenges he faced throughout 2022, stemming from a demoralizing loss at the Australian Open. Nevertheless, he made an impressive comeback in the early stages of 2023, solidifying his position in the top five of the ATP rankings.
Recently, he achieved one of his finest victories of the season by defeating the defending champion and world #1, Carlos Alcaraz, in the semifinals at the US Open. The victory he secured against the top-seeded Carlos Alcaraz, with a scintillating performance, was precisely the outcome he had been fervently hoping for at the start of this campaign.
Not only had he been decisively outperformed and left seemingly clueless by the Spaniard on two occasions earlier in the year at the Indian Wells Masters and Wimbledon, but Medvedev had also expressed some dissatisfaction with Alcaraz assuming the role of the primary rival to Djokovic in the tennis world this year.
He had mentioned feeling overshadowed by the emerging Djokovic-Alcaraz rivalry and had expressed a desire to reclaim some of the spotlight for himself.
"Everyone is talking about a (Carlos) Alcaraz vs. (Novak) Djokovic final, that doesn't irritate me at all. Their matches are great for tennis. I do think we still talk about me. The goal is, after this US Open, that we talk about me," he declared before his first match at the US Open.
Medvedev is now poised to compete in his fifth Grand Slam championship match, a record for a Russian player in terms of appearances in title showdowns at this level.
In contrast to some of the non-Big Three winners in recent times such as Dominic Thiem, Marin Cilic, and Alcaraz, the Russian #1 did not have the privilege of facing a non-Big Three player in the championship matches of majors.
However, to his credit, he secured one victory by convincingly defeating Djokovic in straight sets at the US Open, and he came remarkably close to defeating Nadal in straight sets at the Australian Open.
These performances are noteworthy, considering that no other non-Big Four players have ever managed to beat Djokovic or Nadal in straight sets in a Grand Slam final.
The current Miami Masters champion has demonstrated remarkable consistency in hardcourt grand slams in recent years. Between 2019 and 2021, he reached two finals and once made it to the semifinals at the US Open. Additionally, he was a contender in consecutive editions of the Australian Open, featuring in the championship matches in both 2021 and 2022.
The challenges presented to Djokovic at this year's US Open simply didn't meet his usual standard for testing himself. The player who holds the record for the most Grand Slam titles won encountered only one top-10 player on his path to the final. Furthermore, his semifinal opponent was Ben Shelton, who had made his main-draw debut at this level just 12 months ago.
As anticipated, he managed to secure victories quite comfortably in all but one match, where he faced a challenge against Laslo Djere, ultimately earning his place in yet another Grand Slam final.
While his opponent, Medvedev, will be competing in his fifth championship match at this level in his career, this will mark Djokovic's fourth final of the season alone. He had taken the driver's seat in the race for the most Grand Slam titles won after clinching the trophies at the Australian Open and the French Open.
However, his pursuit of a calendar Grand Slam was thwarted when he lost a five-setter to Carlos Alcaraz in the Wimbledon final just two months ago.
Given his proficiency on hard courts and his prolonged dominance at this level for over a decade, it's quite surprising that the current world #2 has encountered more setbacks than triumphs at the US Open.
He hasn't claimed a title in this tournament since 2018 and has endured six losses in the championship matches. This represents the highest number of runner-up finishes he has accumulated in any Grand Slam.
The three-time former US Open champion currently boasts an incredibly impressive record of 26 wins and just one loss on outdoor hard courts this year. Notably, that single defeat came at the hands of Medvedev in the semifinals of the ATP Dubai.
The last and only time he completed a season with just one loss on this surface was back in 2011 when he achieved a remarkable record of 40 wins and one loss.
During that memorable season, he accomplished the seemingly impossible task, at that time, of defeating Federer and Nadal in consecutive matches en route to claiming his maiden US Open title.
Head-to-head: Novak Djokovic leads 9-5. Daniil Medvedev enters this clash in a stronger position, having reached his peak at the right time, particularly evident in his semifinal performance against Carlos Alcaraz.
This is something Djokovic has yet to achieve in this campaign, mainly due to the relatively lesser challenges he has faced.
The level of play that Medvedev displayed in a couple of sets against Alcaraz surpassed anything Djokovic has shown so far in this tournament.
Combined with Medvedev's proven ability in this matchup under these conditions, it's expected that he will pose significant challenges for Djokovic, who is also facing some pressure as he seeks to equal Margaret Court's record of 24 Grand Slam titles.
For some reason, Medvedev seems to thrive in this matchup only when Djokovic is ranked at #1. Notably, all of his five wins against Djokovic were achieved when the Serbian was holding the top spot in the world rankings. In contrast, he has yet to secure a victory against Djokovic when he was not ranked #1 (with a 0-6 record).
It will be intriguing to determine whether this pattern is merely a coincidence or a significant factor that influences Medvedev's mentality in these high-octane matches.
Following his victory in their recent encounter in Dubai earlier this year, Medvedev remarked: "Actually, I saw one interesting stat that I am 5-3 against Novak when he's #1. I'm 0-6 when he's not #1. I'm like, 'Stay #1 as long as you can. If I can play you when you're #1, it will be better.'"
