All five defendants pleaded guilty to conspiracy to steal.
The gang carried out 22 thefts across the north of England, Wales and the Midlands between August 2008 and August 2010.
Construction machinery with an estimated value of up £2m was smuggled out of the country.
As well as breaking into construction sites, they also set up bogus companies to hire plant and make off with it, prosecutors told Bradford Crown Court heard.
Judge Jonathan Durham Hall sentenced gang leaders Mark Lambert, 46, of Amber Wharf, Dock Lane, Shipley, and Peter Green, 46, of Highfield Drive, Birstall, to three years nine months in prison.
Three co-conspirators each got 15 months. They were: Sharon Pearson, 39, of Capa Terrace, Odsal; Matthew Wheatley, 22, of Mark Close, Idle; and David Colley, 43, of Chapel Street, Netherton, Huddersfield.