Trainer Chris Waller has two colts attempting to mirror Vanbrugh's jump from midweek winner to Group Three victor in the Gloaming Stakes.
Waller is looking for back-to-back wins in the race after Vanbrugh won last year's Gloaming on his way to winning the Group One Spring Champion Stakes.
High Mist and Veladero won separate midweek races at Warwick Farm over 1600m in their last starts before the Gloaming.
Vanbrugh had the same lead-up last year.
High Mist's Jockey Hugh Bowman was suspended for careless riding after the Warwick Farm win, paving the way for Glyn Schofield to take the ride at Rosehill on Saturday.
High Mist's return to midweek racing came after he was beaten by Swear in the Group Three Ming Dynasty when he didn't see daylight until it was too late.
"He was a tad unlucky the start before his win so he has his crack now at a Group race again," Schofield said.
"He's got the runs on the board and he looks like a quality horse."
It is 10 years since Waller won his first Group race with All Black Gold in the Gloaming.
At the time it was his biggest win in racing, but since then he has shattered Sydney's training records for winners and prize money.
High Mist is a $3.80 chance for the Gloaming behind $3.50 favourite Prized Icon, a Group One winner as a two-year-old who is trained by James Cummings.
Hawkes Racing-trained Swear is at $4.80 and Veladero is an $8 chance.
Schofield will also ride outsider Cellarman for Waller in the Group Two Stan Fox Stakes and Listed Reginald Allen Quality favourite Smart Amelia for Cummings.
Smart Amelia was fourth first-up in the Group Two Furious Stakes (1200m) when she closed off well late at Randwick on September 3.
"She seems to have trained on from it," Schofield said.
"She's got a low marble again Saturday so she should land a little bit closer to the speed."