Rising British star Jack Draper will play top seed Rafael Nadal in the Australian Open first round with Andy Murray also handed a difficult draw.
Murray faces 13th seed Matteo Berrettini, while Novak Djokovic makes his Melbourne return against Spain's Roberto Carballes Baena.
Emma Raducanu, who has been struggling with an ankle injury, has been drawn against Germany's Tamara Korpatsch.
Raducanu, 20, could face seventh seed Coco Gauff in the second round.
The Australian Open, which is the first Grand Slam tournament of the new season, takes place at Melbourne Park between 16-29 January.
Tough draws await Draper and Murray
Draper, 21, emerged as one of the rising stars on the ATP Tour last year and the left-hander has continued his rapid progress this season by reaching the Adelaide semi-finals.
But his debut in the main draw at Melbourne Park could not have been much tougher.
Nadal, 36, is the defending champion and, although he has struggled with injuries and lost his two matches so far this year, remains a daunting prospect for most opponents.
However, the 22-time major champion would also probably not wish to start against a young talent who possesses the power and confidence of 40th-ranked Draper.
Former world number one Murray will also be cursing his misfortune.
The 35-year-old Scot impressed earlier on Thursday by beating Australian Alex de Minaur in an exhibition match at the Kooyang Classic, saying afterwards he hoped for a kind draw at Melbourne Park.
Instead he was pitched against Italy's Berrettini, whose big serving troubles most opponents and who reached the semi-finals last year.
What about the other Brits?
Raducanu, who shocked the world by winning the 2021 US Open as a teenage qualifier, suffered what she described as more bad luck when she rolled an ankle in Auckland last week.
It led to doubts over whether she would be fit to play in Melbourne, but she has been practising on court - albeit looking somewhat tentative at times - in the past few days.
Raducanu is ranked one place below Korspatch at 75th in the world, but the 27-year-old German has never won a main-draw match at a major.
Cameron Norrie, Britain's highest ranked player and the 11th seed, starts against French wildcard Luca van Assche, while 25th seed Dan Evans faces Argentina's Facundo Bagnis.
Another difficult draw for a British player saw Kyle Edmund - a semi-finalist in 2018 but on the comeback trail after three knee surgeries - plays Italian 15th seed Jannik Sinner.
Harriet Dart, the only other Briton in the women's draw, starts against Swiss 32nd seed Jil Teichmann.
Djokovic learns his opponent on return
Nine-time champion Djokovic missed last year's event after being deported from Australia in a row over his vaccination status and returns on the back of winning the Adelaide title last week.
The 35-year-old Serb, who is also bidding for a 22nd major title which would equal Nadal's men's record, has only lost one of his past 25 matches.
Seeded fourth, Djokovic would not face Nadal until the final - but could face home favourite Nick Kyrgios in the quarter-finals.
In the women's draw, world number one Iga Swiatek, who reached the semi-finals last year, starts against Germany's recent Wimbledon quarter-finalist Jule Niemeier.
Another eye-catching draw sees Belarus's Victoria Azarenka and American Sofia Kenin - both former champions - meet in the first round.