Up-and-coming sprinter Sessions could get his first taste of stakes company in Friday night's Canterbury Classic.
Darley's number one jockey Kerrin McEvoy, temporarily based in Melbourne, will return to Sydney for the meeting and has been booked to partner the three-year-old.
Trainer Peter Snowden is expected to decide on Thursday whether Sessions will take his place in the Listed race after drawing the outside barrier.
The colt has also been paid up for a 1200m race at Warwick Farm on Saturday and has a kinder draw in five, but if Snowden takes that option Sessions will be ridden by Josh Parr.
McEvoy is already committed to the Australia Day meeting at Caulfield where he will test some of Darley's leading juveniles in the Blue Diamond Previews.
The Canterbury Classic (1100m) has attracted a field of nine including last year's winner Unanimously and comeback galloper Whitefriars who was runner-up in the race two years ago.
He has only raced twice since winning the 2011 Group Two Australia Stakes at Moonee Valley at his subsequent start and finishing unplaced on return in the Razor Sharp Stakes last month.