Brian Smith, Elijah Boswell, Glen Hepburn, Michael Tillotson and Mark Ella were charged with conspiracy to steal after officers discovered that they had stolen or cut cable to be taken away from 11 BT sites across the county between October 2012 and January 2013.
The scrap value of the cable was more than £33,000 with a replacement value to BT of over £50,000.
The gang used large metal keys, only available to BT engineers, and specialist hydraulic lifting equipment to open manhole covers and access the cable which was installed at least 1.5 metres below the ground.
They targeted remote areas, often at night in an effort to avoid detection, but were caught when they were stopped travelling in convoy away from the scene of a cable theft on the A171 Whitby to Scarborough road.
The other theft sites were at Naburn Lane, in Naburn, near York; Speeton, in Filey; the Whitby road in Cloughton, near the Falcon Inn; and Moor Lane, in Murton, near York.
All five had pleaded guilty to all 11 thefts at an earlier hearing at Teesside Crown Court.
Smith, 37, of James Street, York, was jailed for 27 months. His sentence will run concurrently with a nine-year-sentence he also received yesterday for conspiracy to supply Class A drugs in York.
Boswell, 26, of Smithies Lane, Barnsley, was sentenced to two years in prison. Hepburn, 35, of Gaitskell Walk, Leeds, was jailed for two years and three months.
Tillotson, 45, of Airy Hill, Filey, was jailed for two years and nine months and Ella, 39, of Bramham Avenue, York, was sent to prison for 12 months.