Giovani Garrick and Keenan Anderson were linked to 11 cash box raids in three months across Birmingham, Handsworth and West Bromwich.
A gang assaulted or threatened security drivers with weapons as they went to shops, post offices and other premises between April and July last year.
The robbers then fled in a waiting vehicle - which was different on most occasions to try and avoid being traced.
CCTV identified Garrick and Anderson as prime suspects and after arresting the pair in August, officers carried out searches of addresses linked to them and recovered clothing matching the description on CCTV clips. Officers also found two axes in a property connected to Anderson.
The pair admitted conspiracy to commit cash-in-transit robberies and they were sentenced at Birmingham Crown Court on Monday.
Garrick, 23, of York Road, Edgbaston, was jailed for 12 years and 11 months, while Anderson, also 23, of Albert Road, Handsworth, was sentenced to 10 years and nine months.
Detectives are still trying to find another 23-year-old, Dante Kalsi, who is wanted for questioning over the series of robberies.
Despite a previous appeal for information on his whereabouts, he is still to be traced.
DC Tom Simpson, from West Midlands Police CID, said: “This was a sustained crime spree where security drivers were left fearing for their safety. Fortunately no-one was seriously injured but a lot of money was taken.
"We launched a dedicated operation to catch those responsible and enquiries established that Garrick and Anderson were involved. This was backed up by the subsequent searches.
"They were not the only ones involved and we still need to trace Dante Kalsi for questioning. I would urge anyone with information to contact us via Live Chat, or by calling 101."
Garrick and Anderson were convicted of offences in the vicinity of the below locations:
Robbery at supermarket in Rookery Road, Handsworth, on 17 April 2019
Attempted robbery at post office in Rookery Road, Handsworth, on 8 May
Robbery at petrol station in Holyhead Road, Handsworth, on 10 May
Robbery at shop in Soho Road, Handsworth, on 13 May
Robbery at bank in Frederick Street, Jewellery Quarter, on 14 May
Robbery at post office, College Road, Handsworth, on 22 May
Robbery at shop in Queens Head Road, Birmingham, on 31 May
Robbery at shop in Lozells Road, Birmingham, on 4 June
Assault with intent to rob in Oxhill Rd, Handsworth, on 18 June
Robbery at a shop, Birchfield Road, Perry Barr, on 10 July
Robbery at a shop Vicarage Road, Hateley Heath, West Bromwich, on 18 July