"I won the Queenstown Cup down there a few years ago, which was quite exciting. I have won three races there, which I am happy with as I just train for myself," he said.
Dobbs will trek south on Thursday with his entire race team of two and he is hoping for bold showings from the pair.
Well-related mare Emanon is set to contest the Catalyst Performance Clare Memorial Cup (1220m) on Friday, while four-win mare Youneverknow will line-up in the Alexandra New World/NZ Cherry Corp (2030m).
Emanon, a half-sister to Group One darling Legarto, couldn't add to her eight-win haul over New Zealand Cup Week, finishing unplaced in both the Listed Pegasus Stakes (1000m) and Listed Stewards' Stakes (1200m), but Dobbs believes the drop back from stakes grade should be a huge assist for his mare this weekend.
"We went up to Cup Week and all the North Islanders came down and there were some good horses there with the top jockeys, and we just couldn't quite foot it with them," he said.
"At Cromwell she will be back in her class a bit and she should hold her own. Sanu (Toolooa) is back riding her and he has won four on her."
Dobbs is more hopeful than confident with Youneverknow, but he said he has always rated the daughter of Sacred Falls highly.
"We just need a bit of luck with Youneverknow," he said. "I have always had a lot of time for her, she is a nice horse, but she just never has the right sort of run."
Dobbs has Emanon on lease from breeder Warwick Jefferies, with the mare set to return to Jefferies at season's end, and Dobbs is hopeful of getting a stakes result with the daughter of Burgundy before she leaves his care.
While his focus is firmly on Cromwell, Dobbs has circled the Listed Hazlett Stakes (1200m) at Wingatui on Boxing Day as her next big assignment."We will probably keep around down in the South Island. There is another couple of races coming up, including a big race down at Wingatui which could be right for her," Dobbs said.