Dennis, 36, was given a suspended 17-month jail term and banned from driving for five years in 2025.
It followed a guilty plea over the events leading up to the death of his Olympian wife Melissa Hoskins.
Despite the suspended sentence over his head, Dennis was allegedly caught driving with two children as passengers on June 11.
That offence - and the associated offence of breach of bond - landed him before Judge Ian Press, the same judge who sentenced him in 2025.
In the SA District Court on Tuesday, Dennis's barrister told Judge Press that, from every perspective, it would be inappropriate for him to deal with the matter.
At sentencing in 2025, the judge warned the former world champion time trialist that any violation of the driving suspension would be a breach of the bond linked to his suspended sentence and he could expect to be jailed.
Dennis's lawyer conceded Judge Press sentenced Dennis in a fairly orthodox way but the warning about potential inevitable consequences for a breach were framed "in fairly emphatic terms".
"The perception that Your Honour ... might be personally affronted at the fact that - having given an opportunity to a man by way of a suspended sentence and having given the caution or warning of the potential consequences - that that of itself carries with it almost the inevitable outcome," David Edwardson KC told the judge.
Mr Edwardson said it was a sensational case, which has (had) remarkable publicity at so many different levels.
"The bottom line is, we are now looking at a separate and distinct and unique exercise of discretion against a background of intense public interest, pressure, outcome, warnings."
It would also be extraordinary for a sentencing judge to deal with a breach, he said - a claim dismissed by the prosecutor.
The prosecutor also said there was nothing inappropriate about a defendant receiving a standard warning about the consequences of not abiding by a good behaviour bond.
Judge Press said it was happenstance that he had been assigned to the Dennis's breach case.
The two-time Olympic medalist and six-time world champion had agreed to a $100, two-year good behaviour bond in 2025.
His driver's licence was also suspended for five years.
The maximum penalty for driving while disqualified is 12 months in prison.
Dennis could also potentially face 17 months in jail for breaching his good behaviour bond.
Hoskins, herself an Olympian and world champion cyclist, was struck by her husband's vehicle near their home at Medindie, in Adelaide's inner north, on December 30, 2023.
The 32-year-old suffered serious injuries and died in Royal Adelaide Hospital.
Judge Press will announce his decision on the recusal application on September 30.
