Dante Morgan and Chakiah Lambert were sentenced to a combined 23 years behind bars after being found guilty of conspiracy to rob at Wolverhampton Crown Court.
They were part of a gang that carried out a series of raids in the summer of 2018.
The spree began at a house in Solihull on August 4, where an Alfa Romeo was stolen after the keys were snatched from inside.
Ten days later the gang carjacked a mother at gunpoint in Wolverhampton, demanding the keys to her VW Golf while her children were inside.
Sentencing the robbers in Wolverhampton, Judge Jon Butterfield QC explained: "She had only just driven back home and she frantically scrambled to remove her children from the back seat before the car was driven off her drive and away.
"She must have been utterly terrified."
The next day four men - including one armed with a hammer and one with a knife - burst into Tesco Express in Rowley Regis as cash delivery drivers were restocking the store’s cash machine and made off with £71,000 in notes.
"Staff and customers were threatened and put in fear. Over £71,000 was taken," Judge Butterfield continued.
The Golf stolen the previous day had already been fitted with fake number plates and was used as the getaway car.
Police began to close in the next day when the stolen Alfa Romeo activated an automatic number plate recognition camera and was chased by police.
Lambert, 23, lived in West Bromwich at the time while 21-year-old Morgan lived in Oldbury. They and two other men from the car were arrested after a foot chase.
Judge Butterfield said the false number plates on the VW Golf, which was abandoned, were checked for fingerprints and Lambert's palm print was found.
Lambert, of Bibsworth Avenue, Moseley, Birmingham and Morgan, who is already serving a nine-year prison sentence for robbery, were convicted of conspiracy to rob following a trial at Wolverhampton Crown Court.
Mr Kevin Metzger, representing Lambert during the sentencing hearing on Friday, said he was still a young man and had taken the opportunity to do some educational work.
Representing Morgan, Mr Meyrick Williams said it was not suggested he had been in possession of any weapons and argued Morgan should be regarded as lesser culpable.
Judge Butterfield jailed Lambert for 14 years and Morgan for nine years, to run consecutively to his existing sentence.