Denis Shapovalov showed he is ready to challenge for the Wimbledon title by booking his first grand slam semi-final with a five-set win over Karen Khachanov.

The Canadian won the boys' crown in 2016 and is giving himself the best chance of replicating that in the men's draw with an epic 6-4 3-6 5-7 6-1 6-4 victory over the Russian.

His biggest test is now to come as he faces world number one and defending champion Novak Djokovic in the last four on Friday.

But the 22-year-old proved he belongs on the biggest stage, coming from two sets to one down with his trademark flamboyance, and is likely to be a contender at this tournament for years to come.

He is one of two men who made it through to the last eight that have won the junior title.

So it only seemed a matter of time until he made an impact in the men's draw and had got to this point playing some eye-catching tennis, which he brought on to Court One.

He forced four break points at 3-3 in the opening set, which Khachanov was able to wriggle out of, but there was no escape in the next service game as he took the break with a crisp volley after a smart approach.

He quickly served out the first set in his next service game and that appeared the perfect platform for him.

But Khachanov had other ideas and, as Shapovalov's forehand went missing in action, he quickly reeled off four successive games to put a tight grip on the second set.

Shapovalov's level came some of the way back and he regained one break but Khachanov steely averted any further comeback attempt to level the match up.

The third set was a titanic battle with both men peppering winners from the baseline, but it was Khachanov who edged it, stealing a break at 5-5 and then serving it out.

Shapovalov was staring down the barrel but immediately came out firing and dominated the fourth set, reeling off five successive games to win it 6-1 and take the match to a decider.

Khachanov's heart must have sunk at that point, following his gruelling five-set battle with Sebastian Korda on Monday and the last thing he needed was his opponent stepping it up a level.

He almost made a breakthrough at 2-2 but Khachanov recovered from 0-40 to hold but Shapovalov kept coming back and the match was won in the ninth game of the decider.

After squandering three more break points, he finally won his fourth when Khachanov drifted a forehand long, allowing him to serve it out.

"It was super tough, especially in the fifth, missing those break points and then having the craziest game of my life," Shapovalov said in his on-court interview.

"I was in a similar position in the US Open in the quarter-final and I started that fifth set a little bit slow so I told myself I wanted to start quick and play every point as hard as I can in the fifth set. Luck was on my side."