The Australian Open may have kicked off on Sunday, but the Canadians in the tournament will all take to the court for the first time tonight in Melbourne.

Milos Raonic, Denis Shapovalov, Eugenie Bouchard and Bianca Andreescu will all begin their tournament runs in the first major of the year Monday night.

Bouchard and Andreescu will be the first two Canadians on court, with Bouchard following the match between Italy's Fabio Fognini and Jaume Munar of Spain at 1573 Arena. Andreescu will take on American Whitney Osuigwe on Court 15 following a match between Nicolas Jarry and Leonardo Mayer. 

Shapovalov's match against Pablo Andujar will follow directly after Bouchard, while Raonic is scheduled to take to the court against Nick Kyrgios at 3 a.m. ET/Midnight PT.

Bouchard vs. Peng - LIVE ON TSN5 at (approx.) 9 p.m. ET/6 p.m. PT.

Bouchard, whose match will air LIVE on TSN5 at an estimated time of 9 p.m. ET/6 p.m. PT., is looking to build on the momentum she's had over the past seven months. Sitting at No. 193 in the world last June, Bouchard has made her way up to No. 79 entering the Australian Open and is coming off a quarter-final run earlier this month in Auckland. Bouchard also won the women’s doubles tournament in Auckland with partner Sofia Kenin.

On Monday night, the 24-year-old will meet Shuai Peng, who came back from a six-month suspension last month. Peng, who is ranked No. 128, was suspended for trying to change her doubles partner after the sign-in deadline at Wimbledon. She has played in just two tournaments since serving her suspension and retired in her lone singles match - against Kristyna Pliskova on Jan. 1 at the Shenzhen Open.

Should Bouchard advance, she will likely face seven-time Australian Open champion Serena Williams in the second round.

Andreescu vs. Osuigwe - LIVE ON & TSN App at (approx.) 9 p.m. ET/6 p.m. PT.

Andreescu enters the Australian Open with plenty of momentum after reaching the finals in Auckland and breezing through the tournament qualifiers without dropping a set. The 18-year-old from Mississauga, Ont., posted wins over former world No. 1's Venus Williams and Caroline Wozniacki during her Auckland run and has started 2019 with a 10-1 record. Her ranking jumped 46 spots to No. 106 in the world entering the year's first major and will be taking a fellow tournament debutant in Osuigwe. Osuigwe, 16, was given a wild-card spot for the tournament and is currently ranked No. 203. 

With a win, Andreescu would likely be set up for a second-round match against 13th seed Anastasija Sevastova.

Shapovalov vs. Andujar - LIVE ON TSN5 at (approx.) 10:15 p.m. ET/7:15 p.m. PT.

Shapovalov enters this year as the second-highest ranked Canadian in the draw behind Raonic. Ranked 27th in the world, the 19-year-old is seeded 25th in Melbourne and is looking for his first win since October against Andujar. 

Andujar, ranked 82nd in the world, is a clay-court specialist and won the 2018 Challenger de Buenos Aires in November. The 32-year-old, however, has never advanced past the second round of a hard-court major.

Shapovalov, who has exited in the first round of three straight tournaments, reached the second round at Australian Open last year. Should he advance once again, Australian Thanasi Kokkinakis will likely await him in the second round, while a match with No. 1 Novak Djokovic looms if Shapovalov can reach the third round.

Raonic vs. Kyrgios - LIVE ON TSN5 at (approx.) 3 a.m. ET/Midnight PT.

Raonic enters the Australian Open ranked 17th world, but the 16th seed in the tournament has a daunting series opponents ahead of him in his pursuit to top his previous career-best of a semi-final berth in in Melbourne (2016). If the 28-year-old can get by Kyrgios in his opening match, he is projected to face 2014 tournament champion Stan Wawrinka in his next match. 

Raonic reached the quarter-finals at the warm-up Brisbane International earlier in January after a two-month layoff, while Kyrgios went 1-1 in Brisbane for his first win since Oct. 2.

The two have met six times previously, though not since 2016. They have split their career series 3-3, though Kyrgios owns a 1-0 edge on hard courts.