Glyn Schofield has already won four Group One races in his best start to an Australian season.
The jockey will chase another when he partners Boban in Saturday's Darley Classic over the straight 1200m course at Flemington.
"Boban is obviously trying the straight for the first time which is a bit of an unknown," Schofield said.
"He's had a jump-out, his fresh form is pretty good but of course Chautauqua is going to be a hard nut to crack.
"We're taking him on at his preferred trip. It will just be interesting to see how Boban runs. I do think he'll run well, but obviously the race will tell."
Chautauqua is the $1.60 early favourite with Boban at $15 in a 10-horse field which also includes Terravista ($8), Srikandi ($9.50), Lumosty ($13) and Buffering ($15).
Boban won the Group One Emirates Stakes (1600m) at the corresponding meeting two years ago.
Schofield said Boban got a bit lost in the first half of his recent jump-out down the straight.
"It was only four furlongs (800m) so it wasn't a testing trial for him, but he certainly got going a little bit late," he said.
Boban takes aim in the Darley Classic with a view to a possible trip to Royal Ascot next year.
"He's got his toe in the water to test with Royal Ascot in mind next year. There wasn't a great deal of options for him in the spring after those couple of Group Ones he contested early, so he's had a good freshen," Schofield said.
"He tries the straight and you never know. He does possess a good turn of speed, whether he can do it off a straight-track and a fast tempo, we'll see."
Chautauqua will be out to go one better than last year's second to Terravista in the Darley Classic.
So far this spring the Hawkes Racing-trained gelding has been a dominant winner of the McEwen Stakes, Gilgai Stakes and Group One Manikato Stakes.
"His win in the Manikato was so dominant and his straight form probably looks as good if not better, so he'll be very hard to beat." Schofield said.
Dwayne Dunn, who missed Chautauqua's Manikato win through suspension, is back aboard on Saturday.
Boban won the Group One Memsie Stakes (1400m) first-up this campaign before a close fourth in the Makybe Diva Stakes (1600m).
Schofield also netted Group One wins this spring in Sydney on Kermadec in the George Main Stakes and Vanbrugh in the Spring Champion Stakes, while he won the Coolmore Stud Stakes last Saturday down the straight at Flemington on Japonisme.
All have been trained by Waller.