Willy Jimmy's chances of cementing a Doncaster start have been dealt a blow by a wide barrier in a qualifying race at Rosehill on Saturday.
Another stumbling block could be his stablemate Skyerush who will start from barrier one in the Group Two Ajax Stakes (1500m), the winner of which is exempt from ballot and penalty in the $2 million Doncaster Mile on April 20.
Willy Jimmy has the limit weight of 52kg and is 41st in the ballot order for the Doncaster. The seven-year-old needs to win the Ajax from barrier 17 or the Doncaster Prelude to join Guy Walter's Doncaster team which doesn't include Skyerush.
The mare's goals are a defence of the Group Two Emancipation Stakes on the final day of the Sydney carnival before she gets ready to take care of some unfinished business in Brisbane.
Skyerush finished a fighting second to Pear Tart in the Tatt's Tiara last June and the fillies and mares race is once again her Group One target.
Her first-up win in the Liverpool City Cup has Walter confident she is on track for another big showing in the Ajax.
"I can't fault her," Walter said.
"She has done extremely well since the Liverpool City Cup and is just a lovely mare to do anything with.
"She has been under-rated. She has always run well at the top level but the Doncaster is not the race for her."
Walter is hoping it is the race for Willy Jimmy if he can force his way into the field.
In his only attempt at the famous Randwick mile in the 2011 Epsom Handicap, Willy Jimmy ran fourth behind outstanding mares Secret Admirer, Pinker Pinker and Red Tracer.
After Willy Jimmy ran fourth in this year's Group Two Apollo Stake, Walter sent him to Melbourne for the Blamey Stakes where he finished midfield, two lengths from dead-heaters Budriguez and Puissance De Lune after a slow start.
"He had a hard run in the Blamey but I'm hoping Rosehill will suit him better off a good speed," Walter said.
In 2005, Walter claimed a history-making trifecta in the Doncaster but a repeat would depend on Willy Jimmy joining Group One winners Streama and Appearance in the field.
Appearance's win in last Saturday's Coolmore Classic has earned her a half kilogram penalty and she and Streama will both carry 52.5kg.