When Milos Raonic and Denis Shapovalov saw the official draw for the 2018 Australian Open on Thursday, likely neither Canadian was thrilled.
Raonic, the 23rd ranked player on the ATP Tour, is seeded 22nd in Melbourne and has an easier start than Shapovalov, drawing Slovakia's Lukas Lacko in the opening round. Assuming he wins his first two matches, Raonic could face 13th seeded Sam Querrey in the Round of 32 before a likely quarterfinal match against Roger Federer, the second seed and defending champion who has five Australian Open titles on his illustrious resume.
WATCH: Shapovalov shows basketball skills, moving for hard courts the hardwood
Federer and Raonic have met 13 times previously with Federer owning a 10-3 head-to-head record against Raonic, including a 2013 victory at the Australian Open. However, Raonic beat Federer in two of their last three meetings, including a straight sets victory at the 2016 Brisbane International.
The 27-year-old Raonic enters this year's open seeking his first win after losing his first match of the new year down under in Brisbane two weeks ago. In an upset, he fell to wild card Alex de Minaur in straight sets, 6-4, 6-4.
Shapovalov, ranked 50th in the world, opens against fellow Next Gen player Stefanos Tsitsipas of Greece. If he gets past Tsitsipas, the 18-year-old Shapovalov likely faces Jo-Wilfried Tsonga, the 15th seed who is also the 15th ranked player in the world.
Here are your intriguing #AusOpen draws in full 🤗
— #AusOpen (@AustralianOpen) January 11, 2018
Women's singles: https://t.co/EUvJBQjeHL
Men's singles: https://t.co/7ceZqRgWki pic.twitter.com/VC6i8bylUf
That potential difficult second-round match is an intriguing one based on Shapovalov's 6-4, 6-4, 7-6 upset victory over Tsonga last September in the Round of 64 at the U.S. Open.
Third-seed Grigor Dimitrov is a possible opponent for Shapovalov should the teen sensation reach the quarterfinals.
Shapovalov is 1-2 in match play so far in 2018. He dropped his opening-round match against Kyle Edmund at the Brisbane International and then lost to Juan Martin del Potro Wednesday in the second round of the ASB Classic in New Zealand.