Denis Shapovalov produced some of his best tennis in a high-intensity, high-drama showdown on a humid afternoon in Sydney, but it wasn’t enough to take down one of the toughest challenges in tennis: 7-time Australian Open champion Novak Djokovic… in Australia. The Canadian fought valiantly, but succumbed 4-6, 6-1, 7-6(4) after two hours and forty minutes of high-quality tennis.

In what was Canada’s second match of the best-of-three tie against Serbia, Shapovalov came in with his back against the wall as the earlier defeat of Félix Auger-Aliassime had Canada down 0-1 going into the crucial rubber.

The first set saw Shapovalov rise to the Djokovic challenge with aplomb. Coming into the match with a discouraging 0-4 record against the 16-time Grand Slam champion, the Canadian played with the familiar confidence and free-flowing tennis that has characterized his last several months on tour. Although he finished runner-up to Djokovic in his first Masters 1000 final in Paris just over two months ago, both tactical and technical changes in the Shapovalov playbook were paying their dividends in Sydney on Friday afternoon.

Hitting his spots brilliantly on serve and hanging in the longer rallies with one of the world’s best defenders, Shapovalov kept proceedings tight with Djokovic until a pivotal break point in the ninth game swung the way of the Canadian, sealed with a surprising – but delectable – drop-shot winner from the baseline. One game later, and Shapovalov led the World No. 2 by a 6-4 set.

The second set threatened to get away from Djokovic, as Shapovalov’s level continued to electrify a largely Serbian-partisan Ken Rosewall Arena. That electricity short-circuited the crowd, however, after a 10-minute game on the Djokovic serve early on culminated into a quick break of the Shapovalov serve and subsequently set off a boisterous crowd. Frustrated by the mid-point noise levels, the Canadian was quick to surrender his focus – and with it, the set.

Both players brought out their competitive best in the final set, with each threatening to make inroads on the others’ serve but ultimately digging out tough holds. The first slip-up, literally, would be Shapovalov’s as a crucial 30-30 point in the ninth game would go the way of Djokovic as the 20-year-old southpaw would slip on his way up to a volley.

A break would immediately follow but the story wasn’t finished there. Exceptional defensive play would help Shapovalov orchestrate his own break to level the score and the match was soon headed to a tiebreak. Djokovic, who famously hit zero unforced errors across three tiebreaks against Roger Federer at Wimbledon last year, would ultimately buckle down in the same way against Shapovalov, who himself boasted an exceptional 7-1 final-set tiebreak record. On his fourth match point, the match was his, and the tie – Team Serbia’s.

Canada’s 2020 ATP Cup campaign comes to an end.

(Feature photo: ATP Tour)