Roberto Parma, 54, was sentenced to six year and seven months in prison for exploiting the UK duty suspension scheme.
Parma, owner of Italian-based importer I Nobili UK Ltd, used the same delivery documents many times and avoided paying duty by diverting wine from the bonded warehouse.
Alberto Mori, 53, owner Of London wine merchant Soldo UK Ltd, was jailed for seven years for working with Parma to sell the wine illegally through a network of UK wholesalers.
HMRC investigators found that Parma’s company provided cover for the fraud from Italy via online Skype.
The firm orchestrated the movement of wine from Italian warehouses and gave code words to drivers to use when picking up the loads to avoid paperwork landing in official hands.
David Margree, assistant director of criminal investigation at HMRC, said: “The sole intention of importing this wine was to rip off the honest taxpayer to line their own pockets. These men thought they would use crafty code words and complex chains to avoid detection, but HMRC was able to detect and stop this scam.
“HMRC will not stand by while criminals try to cheat the system. The message is clear - HMRC will find you, and you will go to court.”
Parma and Mori were arrested in July 2009 after the discovery of more than 114,000 litres of wine during a search. HMRC investigators realised the scale of the crime after finding records on a company computers and on a memory stick mapping out the fraud.
Parma and Mori skipped bail and returned to Italy, but were tracked down by Italian police and extradited to the UK in 2012 to stand trial. During the arrest more than £58,000 of cash was seized. Both men were found guilty on two counts of evasion of excise duty and VAT.
Confiscation proceedings are underway.