Five of Darley's most talented three-year-olds will be split across three races in two states on Saturday with Sidestep leading the charge in Sydney.
The Golden Slipper runner-up will resume alongside stablemate Kuroshio in the Group Three San Domenico Stakes at Rosehill.
In Melbourne, Safeguard will resume in the Group Three Vain Stakes while Montsegur and Metastasio tackle the Group Three Quezette Stakes for fillies.
All are over 1100 metres and deciding which horse runs where is determined as much by trainer Peter Snowden's overall spring plans as the suitability of the individual assignments.
Sidestep is being aimed at the Group One Golden Rose, via the San Domenico and the Run To The Rose.
Safeguard will be geared towards the sprints in Melbourne, swaying Snowden to begin his campaign at Caulfield.
"For mine, it suited Sidestep looking towards the Golden Rose," Snowden said.
"There's not much point having one run in Melbourne and then coming back to Sydney for the next one. He can be placed perfectly up here for those three races including the Golden Rose.
"Safeguard, if he runs well Saturday, the Danehill (Stakes) is there in three weeks time.
"It's not just one run, you're looking at the next two or three runs."
Sidestep is the $3 favourite for the San Domenico.
A half brother to Skilled and Ambidexter who were both effective over 1600 metres, Snowden says Sidestep is sharper and more athletic than that pair.
As a juvenile he showed early promise with two stakes placings but his path towards the Golden Slipper took an unexpected turn when he dislodged jockey Corey Brown during the Todman Stakes.
"We had a plan he was going to have two runs into the Slipper but when Corey fell off him at Rosehill it meant I had to back him up the next week to qualify," Snowden said.
"He won that and had to back up again the next week.
"He had three runs in three weeks and for a two-year-old so early in his preparation it tells you he's above average.
"We'll see what happens on Saturday. I'd like to think he can go on with it."
Stable jockey Kerrin McEvoy will ride for Darley in Melbourne where they have runners in four stakes races, opening the door for Tommy Berry to partner Sidestep for the first time.
Berry celebrated his first Group One win on the Snowden-trained Epaulette in last year's Golden Rose but the young jockey turned foe when he teamed up with Gai Waterhouse to win the Slipper aboard Overreach, relegating Sidestep to second.
Christian Reith has been booked for Kuroshio ($9) who looks the likely leader from his inside draw.