Keith, former chief executive of Derby County Football Club, ex-finance director Mackenzie and former director of football Mackay were all handed prison sentences at Northampton Crown Court after it was found that they claimed "secret commission" in the deal.
Keith, 41, of Abingdon, Oxfordshire, was sentenced to 18 months after previously being found guilty of falsifying documents when he and his associates bought the club for just £3 in 2003.
Mackenzie, 55, of Burton Road, Derby, and 53-year-old Mackay, of Fife, Scotland, were each jailed for three years after they were found guilty of fraud.
David Lowe, their legal adviser during the takeover, was convicted of helping to launder £81,895 of the £440,625 the trio tried to claim as a brokerage fee. He was jailed for two years today.
Keith, Mackenzie and Mackay were all disqualified from being company directors - Keith for three years, and the other two for five years.
The court heard that the trio claimed "secret commission" of
£440,625 after arranging a £15 million loan for the cash-strapped club from a Panama-based corporation.
It was claimed they used the loan as a "carrot" for the club, convincing administrators to sanction the takeover.
During the trial, jurors were told that Derby County, nicknamed the Rams, were struggling in 2003 following their relegation from the Premier League the previous year.
The Pride Park club owed more than £35 million and had been put into receivership by the Co-op Bank, the court heard.