After a somewhat routine win for Serbia in the first singles match of the day, with Serbian No. 2 Dusan Lajovic outdoing Canadian No. 2 Felix Auger-Aliassime in straight sets, 6-4, 6-2, the stage was set for a battle between the two nations' No. 1 players, Djokovic and Shapovalov.
While the first match of the day was a first-time meeting, Djokovic and Shapovalov were very familiar - they had played four times before, all in 2019, and not only had Djokovic won all four of those previous encounters, he had won nine of their 10 previous sets, too.
The two players stayed on serve through the first eight games of their fifth meeting, which is when Shapovalov drew first blood, breaking for 5-4 and then swiftly serving out the opening set.
Djokovic retaliated with a 6-1 second set, and after the two again stayed on serve through 4-all in the third set, things heated up - Djokovic got what seemed like the crucial break for 5-4 and a chance to serve out the match, but Shapovalov just wouldn't give in, breaking right back to even the decider up at 5-all. The two then held to send it to a third set tie-break.
That's when Djokovic shifted into another gear, grabbing the mini-break in the very first point and racing out to a 5-1 lead by the changeover. Shapovalov closed the gap but the World No. 2 held on to win the breaker, 7-4, and close out the two-hour-and-40-minute battle.
"This is the closest match that I have ever played against him," Djokovic said in his on-court interview. "The match was so close it could have gone a different way, easily. He was playing terrific tennis. I want to give a huge round of applause and credit to him for playing and fighting so well."
Despite coming up just short, Shapovalov saw the positives from the match.
"It's another step for me, showing me that I'm right there with these guys," the World No. 14 told ATPTour.com. "Honestly, I was a couple points away from taking the match. I think I'm at a really good position. Hopefully I don't stop here. Hopefully I can keep going."
Serbia ended up winning the doubles match for a 3-0 sweep, with Nikola Cacic and Viktor Troicki cruising past Canadian duo Peter Polansky and Adil Shamasdin in straight sets, 6-3, 6-2.
Djokovic is 3-2 head-to-head against Medvedev, though he’s lost their last two meetings, at Monte Carlo and Cincinnati last year. He’s 2-1 against Khachanov, the loss coming in the final of the Masters 1000 event in Paris in 2018. Lajovic is 1-1 against Medvedev and 2-0 against Khachanov.