In a request to Ontario Superior Court, city resident Paul Magder argues Ford spoke to, and voted on, an issue in which the mayor had a personal financial stake.
"(Ford's) conduct was not inadvertent or mere error in judgment," the application states.
"It was flagrant and deliberate."
The issue arose almost two years ago when Ford, who was then a councillor, used his office stationery to solicit donations for his private football foundation.
In August 2010, the city's integrity commissioner found that Ford had violated the code of conduct for councillors.
The commissioner recommended he pay back $3,150 in donations, some of which had come from lobbyists who did business with the city.
Council adopted the commissioner's findings and sanction in a resolution Ford voted against — but, despite half-a-dozen reminder letters from the commissioner, he never made the repayments.
In February, council took up the matter again at the request of the integrity commissioner, but this time, councillors decided Ford did not have to repay the donations.
"To ask for me to pay it out of my own pocket personally, there is no sense to this," Ford said during the Feb. 7 debate.
"The money is gone; the money has been spent on football equipment. That's how this foundation works and I'm very proud of it."
By speaking to and voting on the matter, Ford violated the provincial Municipal Conflict of Interest Act, according to the court application.
Magder, a senior executive with a high-tech firm, said enough is enough.
"I don't want to see any more of that kind of stuff going on," Magder said.
"Respect for taxpayers means respect for the law."
The claim has yet to be proven or tested in court and Ford, who has yet to file any defence, was not available to comment.
However, his spokesman, Chris Christopoulos, said council had already put the matter to rest and the mayor's office had no further comment.
"Council decided on this issue at its February meeting," Christopoulos said.
High profile lawyer Clayton Ruby, who filed the application on Magder's behalf, said it was obvious Ford simply didn't want to repay the money but he should have stayed out of the debate.
"He should not have spoken and he should not have voted," Ruby said.
Twice before Ford's 2010 letter, the application states, the city's integrity commissioner had warned him against using city resources to ask for money for the foundation.
"If he was a brand new councillor, a novice, I'd say, 'OK, maybe there's a misunderstanding'," Ruby said.
"But he's declared conflict of interest on issues over and over again from time to time (but he) just doesn't on this one."
The matter is due in court March 23 where it's expected Ford's lawyer will ask for time to prepare.
Ford has frequently found himself the subject of unflattering headlines.
Last fall, the mayor admitted losing his cool in a 911 call he made after being confronted by a comedy crew in his driveway.