MILAN — Canada's Denis Shapovalov dropped his final match at the Next Gen ATP Finals, losing in five sets to Russia's Andrey Rublev on Thursday.

Rublev, the tournament's top seed, won 4-1, 3-4 (8), 4-3 (2), 0-4, 4-3 (3) in a match that took two hours and one minute.

Shapovalov, from Richmond Hill, Ont., converted on just three of the 13 break points he had, though nine of his missed opportunities came in sets that he won.

Rublev converted both of his break point opportunities.

Shapovalov had eight aces to Rublev's two and just three double-faults to Rublev's six. But the Russian made the most of his opportunities in the tiebreaks to pick up his second win of the tournament and advance to the semifinals.

Shapovalov was eliminated after finishing the round robin 1-2.

At 18, Shapovalov was the youngest player in a field that includes eight of the best 21-and-under players on the ATP Tour.

The tournament continues through Saturday at the Fiera Milano stadium.

Shapovalov reached a career-high ranking of No. 49 last month. He currently holds the No. 51 position.