They targeted small shops and bookmakers and stole thousands of pounds in the series of armed robberies.
Dramatic scenes captured on CCTV show the masked offenders attacking stores armed with an axe, knife and incapacity spray.
The four defendants admitted their parts in separate offences. In total, eight robberies were carried out between September 24 and October 8 2016.
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Lee Frederick Cole, aged 26, of Allen Road, Rushden, who snickered, grinned and yawned as his offences were read out, was sentenced to six years and eight months.
Brett Stuart Trevor, aged 25, of Church Mews, Judith Road, Kettering, pleaded guilty to a single count of joint robbery committed on 8 October 2016. He was sentenced to 44 months.
Two others, who cannot be named for legal reasons, also pleaded guilty to the conspiracy.
A 17-year-old boy was sentenced to 50 months in youth custody and a 16-year-old boy pleaded guilty to a single count of joint robbery committed on 8 October. He was sentenced to 38 months.
The 16-year-old also pleaded guilty to a separate offence of armed robbery where a handgun was used to scare staff and steal money at Ladbrokes in High Street, Kettering on January 10, 2017.
The spree of robberies, which were mostly carried out by Cole and the 17-year-old youth, hit four bookmakers and four convenience shops across Raunds, Wellingborough, Kettering and Thrapston, and were carried out in near-identical fashions.
Lisa Hardy, speaking for the prosecution, described the first robbery on September 24 involving three men. She said: "They targeted bookmakers and small shops at times when only two or three members of staff were in.
"These were confident men entering the premises and the CCTV shows the sheer audacity in their actions. They walk in quickly and clearly armed.
"They brandish an axe, knife and incapacitating spray and threatened the staff. One of the men launches himself to the till and literally leaps over the counter. He uses the axe to attack the till, take the contents. Then they all run out."
On one night, a robbery attempt was foiled when staff at a bookies locked their doors. Twenty minutes later, the group later hit a One Stop Shop around the corner.
During an incident at a Co-op in Hallwood Road, in Kettering, one of the defendants can be seen on CCTV jumping over the counter wielding an axe and demanding the shop assistant open the till.
A second offender is seen running after a second member of staff and spraying from a canister he was holding. The staff member managed to lock herself in a staff room and dial 999.
The terrified assistant can be heard on 999 audio alerting police to the ongoing incident in the store.
The defendants were arrested on October 8 when, between 8.45pm and 9.45pm, robberies were committed at two Co-ops in Kettering.
At about 9.45pm a gold-coloured Renault Clio matching a partial registration of the car seen leaving one of the robberies, was captured on CCTV arriving and fuelling up at Ridge Close service station, Kettering.
Police pursued the car along the A14 and into Cambridgeshire. During the pursuit, items were seen to be thrown from within the car. The car then lost control and came to a stop following a collision.
Two of the defendants were arrested attempting to flee the scene and a further two were arrested having been found hiding in bushes.
Detective Inspector Helen Knight, from CID, said: “The level of violence shown by these offenders was exceptionally frightening for the members of staff involved, who had no way of knowing whether or not the offenders would direct the weapons towards them.
"These custodial sentences reflect the seriousness of the offences committed and the necessity to protect the public from these particular individuals.
"This was a fast-moving investigation that painstakingly gathered and analysed evidence, worked in partnership with local retailers and the Retail Crime Initiative. On the evening of October 8, it was excellent police teamwork that ensured the offenders were pursued and arrested bringing this series of robberies to an end.
"Northamptonshire Police will always robustly investigate such offences and. even when the offenders go to great lengths to conceal their appearance, they will be brought to justice.”