He saddled Harry Topper to win the 2013 Charlie Hall Chase at the West Yorkshire track.
And top novice chaser Rocky’s Treasure could not have been more impressive when winning at last month’s Charlie Hall meeting before following up at Doncaster last weekend under David Bass.
Now he is considering Wednesday’s feature Rowland Meyrick Chase for the progressive Wanderin Star.
The seven-year-old has won two of his three starts this season, most recently sauntering to a 14-length victory at Bangor on December 1. He began the year with a 22-length success over the same course and distance on October 3.
“I need to have a look at the race before I decide whether to run, as he will also be entered for Kempton the following day,” said Bailey whose exciting prospect Vinndication won at Ascot yesterday.
“His two wins this season have been very impressive. It is hard to judge what they are really like, but I can’t complain about what he has done so far. He has earned a step up in class for a race like the Rowland Meyrick.”
This three mile plus test could also feature 2017 Grand National hero One For Arthur.
Sixteen horses – headed by Phil Kirby’s Lady Buttons – have been entered for Thursday’s Castleford Chase .
The field includes defending champion Just Cameron who won this contest 12 months ago for Middleham trainer Micky Hammond and jockey Joe Colliver.
Another Middleham entry of note is Ben Haslam’s Bouvreuil after the horse’s win at Wetherby earlier this month.
Meanwhile Sue Smith could be represented by Cracking Find, another horse with course form.