Andrew Munday, 38, caused a loss to the former X Factor judge’s company of nearly £2.4 million during the fraud campaign spanning seven years.
Dawson’s company suffered damages in the region of £1.08 million as father-of-two Munday siphoned money from their accounts and into his own.
The married gambling addict, of Moulton, Northamptonshire, was sentenced to five years and eight months’ imprisonment on Wednesday after admitting six counts of fraud by false representation and three of money laundering.
Judge Rupert Mayo told Northampton Crown Court: “The individuals who trusted you with their bank sign-in details and therefore trusted you with their hard-earned wealth have been emotionally harmed by the abuse of trust which you perpetrated.”
Munday used the illicit gains to finance his habit, live a “lavish lifestyle” with exclusive membership at Tottenham Hotspur and buy Star Wars and football memorabilia including signed Paul Gascoigne shirts.
The fraudster transferred £1.6 million from Ora’s company into his own account and caused a total loss to the firm of £2,390,747 while an accountant at now defunct Blue Cube Business Ltd.
Former England rugby international Martin Bayfield’s firm Six Ten Media and songwriter V V Brown were also victims of the network of frauds between March 2009 and April 2016.
In a victim impact statement, Brown said she was left feeling “numb” after hearing of the fraud by the seemingly “charming and loyal” perpetrator, who she believes “ruined a lot of people’s lives”.
Bayfield said the crime caused him “mental stress” and Munday “stole any degree of spontaneity our hard-earned money might have provided”.
Munday, who was made bankrupt in 2006, also used the money to buy three properties outright, including one beside Collingtree Park Golf Club.
He also purchased expensive watches and jewellery.
Munday has made efforts to pay back the clients but they are currently facing a £710,000 shortfall.
Prosecutor Simon Davis said the first fraud spotted by Munday’s employers was on Ora’s company, Ora Multi Services (OMS), but this was revealed to be the “tip of the iceberg”.
Munday had told OMS tax payments were due to HMRC but provided the destination for the funds as Brown’s bank account.
He used Brown’s account to launder money into his own and used it to pay other people’s tax bills and for transfers to Tottenham Hotspur, where he had executive membership under the name Munday The Gambler & Sons.
Munday also used the HMRC ruse against A Question Of Sport captain Dawson and his company, Decidedly Dawson Ltd, as well as Bayfield’s.
Mr Davis said: “He was considered a hard-working and trustable employee. However, he was living a lie.
“The defendant spent the money on a lavish lifestyle, real estate and also gambling significant amounts.”
The prosecutor said Bayfield suffered “embarrassment” when, questioned over a bill, he told HMRC that “I paid it”.
But the account number was revealed not to be one for the department.
The court was shown evidence including his fluctuating gambling losses and wins, and told of a photo of Munday, of Earls Close, flaunting a bundle of cash while in his underpants.
In mitigation, Nigel Edwards QC said his client, who has paid back some of his gains, suffered with addiction as the “principal driver” in his life.
“He offers sincere apologies to all those who he defrauded,” Mr Edwards said.