Snooker has not staged a tournament since Trump lifted his sixth ranking event of the season with a 4-3 win over Kyren Wilson at the Gibraltar Open on March 15.
The draw for the Championship League also includes former world champions Neil Robertson, Mark Selby and Stuart Bingham.
With all the big guns avoiding each other in the early rounds, there is the prospect of some major duels for the £30,000 first prize with a Trump and O'Sullivan clash on the cards if both men can progress.
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O'Sullivan has been drawn in Group 10 and will face Chris Wakelin, Michael Georgiou and Kishan Hirani on Friday 5 June. He could face a potential grudge match with fierce Essex rival Ali Carter on Tuesday 9 June if both men win their respective groups.
Trump is in Group 2 and will meet Daniel Wells, Elliot Slessor and David Grace on the opening day of the event on Monday 1 June. He could come across old foe Wilson in the next group stage if he makes a winning start to the event.
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All group matches will be played over four frames and begin at 3pm (BST) each day apart from Friday 5 June which has a 4pm (BST) start.
Under strict government health guidelines, it could provide a blueprint for how the sport will be able to stage the delayed World Championship at the Crucible Theatre in Sheffield which is due to run between 31 July and 16 August.
Championship League details
Monday 1 June
Tuesday 2 June
Wednesday 3 June
Thursday 4 June
Friday 5 June
Saturday 6 June
Sunday 7 June
Monday 8 June
Group Winners’ Stage
Tuesday 9 June
Winner of Group 10
Winner of Group 6
Winner of Group 1
Winner of Group 4
Winner of Group 15
Winner of Group 11
Winner of Group 8
Winner of Group 5
Wednesday 10 June
Winner of Group 12
Winner of Group 2
Winner of Group 7
Winner of Group 13
Winner of Group 14
Winner of Group 3
Winner of Group 9
Winner of Group 16
Thursday 11 June
Winner of Group C
Winner of Group D
Winner of Group B
Winner of Group A
Other details from the Championship League tournament have been revealed by the game's organisers World Snooker Tour:
Social distancing measures in place throughout the venue.
Players seated at least two metres apart during matches.
Players using anti-bacterial hand sanitiser before matches and avoiding handshakes.
Referees endeavouring to keep two metres away from players where possible.
There will be no access for players’ guests.
First aid personnel on site at all times.
World Snooker Tour said: "All players, staff and contractors will be virus-tested prior to entering the venue and will be in isolation until their results are known. Players will require a negative test result in order to enter the venue. They will play all group matches on one day, remaining on site throughout, and will then leave the venue."