"After that, can we win? Maybe not because everybody knows how good Winx is.
"But horses have off days sometimes and if she did then she (Danzdanzdance) is really well and I thought she was very good last start so anything could happen if Winx isn't at her best. And if Winx is too good then I still think we can get some money for sure."
Considering the placings in the Queen Elizabeth are worth A$755,000 for second, A$395,000 for third and even A$180,000 for fourth even the latter would be worth almost as much as winning New Zealand's richest weight-for-age race.
Saturday won't be the first time Bosson has taken on Winx, as he rode Turn Me Loose against her in the Doncaster three years ago.
Even as a jockey, even when you are riding against a great horse, you still appreciate when they are special.
Turn Me Loose wasn't at his best that day and "she gave us all wind burn," remembers Bosson. But that isn't his lasting memory of the wonder mare. "I saw her in the parade ring there a few weeks ago and I was blown away by the look in her eyes," said Bosson.
"She was so focused on what was about to happen it was quite amazing.
"Even as a jockey, even when you are riding against a great horse, you still appreciate when they are special.
"That doesn't mean I don't want to beat her though. I'd love to win this week, we have a farm to pay off," he laughs.
But then the reality of what that moment, being the greatest party pooper in Australian racing history, would really be like.
"It would be weird, very weird."
While Danzdanzdance might leave Randwick a lot richer but without a trophy Bosson has two other group one chances on New Zealand three-year-old fillies who could hardly be more different.
Avantage is the horse who has only lost once in her career and has a strong chance in the $A1 million Arrowfield Sprint while he also rides maiden Clementina in the ATC Oaks.
"She was actually all right last week and the 2400m at Randwick will suit her," says Bosson of his Oaks chance.
"But of all my rides on Saturday I am looking forward to Avantage the most. She had to be really good to win last start and she was only 90 per cent then. She will be better on Saturday."
She will need to be as Avantage is taking on some slick Aussie three-year-olds at their own 1200m game headlined by Zousain, last-start Galaxy fourth placegetter Encryption and the exciting Classique Legend.
The latter shares opening favouritism with Avantage, a very rare position for a Kiwi-trained three-year-old in a group one Australian sprint race. Bosson says Avantage can race up to that honour.
"She has real x-factor, she is so strong and determined," he says.
"She shouldn't have been able to win last start and she has the draw. She can do it."
Bosson's book
Our leading jockey's group one rides on Randwick's huge day.
• R5: A$1 million Arrowfield Stud Sprint, 1200m: Avantage
• R6: A$1 million ATC Oaks, 2400m: Clementina
• R7: A$4 million Queen Elizabeth, 2000m: Danzdanzdance