The cash was not declared as an interest by the Labour-run council
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A property developer donated £5,000 to the Labour Party in Manchester weeks before they won a contract to build a casino complex in the city.
Ask Property Developments donated the money just before Council Leader Richard Leese and deputy Jim Battle gave their project the green light.
Local government watchdog, the Standards Board for England, has opened an inquiry into the donation.
Liberal Democrat Simon Ashley says there is a "conflict of interest."
Mr Ashley, leader of the opposition party in Manchester, said he did not question that Ask had been given the contract on anything other than its merits.
But he said Mr Leese and Mr Battle may have breached the town hall code of conduct, by not declaring the donation as an interest.
"If somebody donates £5,000 to the Labour Party and then gets
a contract five weeks later, I think there's a clear conflict of interest," he said.
"Obviously the board thinks there is something worth investigating.
"Hopefully they will have better luck than me getting answers to the questions I have been asking for many months."
Ask said they had "made donations to the party in order that they can continue their work".
Mr Leese said: "There are rules and as far as I am aware they have all been followed."
The money was given to the Manchester Central Constituency Labour Party on 1 June, and Ask was awarded the contract on 7 July.
The board will investigate three possible breaches of the councillor's code; failing to withdraw from a meeting in which they have a prejudicial interest; bringing their office or authority into disrepute; using their position improperly to confer or secure an advantage or disadvantage.