The gang were involved in the supply of crack cocaine and heroin from Wolverhampton into Kidderminster and Stratford-upon-Avon.
Police chiefs said the convictions were the result of a lengthy and complex investigation lasting 18 months.
Eight of the drugs gang beginning time behind bars were from Wolverhampton and another from Dudley. Albert Morris, aged 20, of Crescent Road, Netherton, was given four years and two months for conspiracy to supply heroin and crack cocaine.
Kingpin Michael Porter, from Adey Road, Ashmore Park, was hit with the heaviest sentence. He was jailed for 20 years in prison after being found guilty of four counts of conspiracy to supply heroin and crack cocaine as well as assault and money laundering.
Christopher Cork, aged 52, of Waterloo Road, got six years and eight months for conspiracy to supply heroin and crack cocaine.
Natasha Frazer, 34, of Chervil Rise, Heath Town, got three years and four months for conspiracy to supply heroin and crack cocaine and money laundering.
Dirk Johannes Howell, 35, of Kingsway Road, Fallings Park, received 22 months and Dale Cooke, 22, of Cadle Road, Low Hill, three years and eight months for the same class A drugs charge.
Junior Evans, 21, of Frost Street, Monmore Green, got four years and eight months and Albert Morris, 20, of Crescent Road, Netherton, Dudley, four years and two months for conspiracy to supply heroin and crack cocaine.
Luke Stephenson, 28, from Hobgate Road, Heath Town, got four years and six months and Michael Carter, 29, of Prosser Street, Park Village, three years and four months for the same offence.
Dawn raids were carried out at addresses across Wolverhampton and Stratford-upon-Avon in June 2015 as part of Operation Southall, which involved West Midlands, West Mercia and Warwickshire police forces.
Detective Chief Inspector Ally Wright, from West Mercia Police, said: "An organised crime group from Wolverhampton saw an opportunity to make money by supplying crack cocaine and heroin in Stratford-upon-Avon and Kidderminster.
"It displaced established dealers and gained a foothold in order to corner the illegal drugs market in the towns.
"Local drug users were then recruited to facilitate the supply of the drugs."
Temporary Detective Sergeant Kris Shore, the leading officer in the case, added: "This was a highly-motivated and organised scheme to peddle misery for gain.
"They were sophisticated, using the rail network and rotating couriers, that they thought would keep the police from their doors. They were wrong and these sentences reflect the hard work and determination of the investigators to protect communities served by Warwickshire Police and West Mercia Police from this sort of exploitation, the harm it causes to the drug users and the resulting crime committed to fund drug habits."
DS Shore added: "I hope that the sentencing handed out by the courts sends out a clear message that the supply of drugs will not be tolerated.
"It is our priority to protect people from harm and bring offenders to justice and tackling illegal drug use significantly helps us to achieve this. We will work tirelessly to disrupt the workings of organised crime groups and make sure that those involved in illegal activity are put before the courts and made to pay for their ill-gotten gains."
Among the other gang members sentenced were Peter Goodwin, 44, of Bidford-on-Avon, Warwickshire, four years for conspiracy to supply heroin and crack cocaine.
Robert Edwards, 51, of South Green Drive, Stratford, got six months for permitting property to be used for supply of class A drugs but was released due to time served on electronic tag. William Wells, 45, of Lodge Road, Stratford, got four years and eight months for conspiracy to supply heroin and crack.
Terry Morris, 47, of Clopton Road, Stratford, got three months for permitting property to be used for supply of class A drugs but was released due to time served on tag.