A security guard feared he would be killed when he was driven at by a would-be robber during a violent spree of attempted raids on vans by a man and a teenager.
Another was injured when he was attacked by the man who was wielding a machete.
However, the pair ended up empty handed because the guards bravely resisted their attempts to seize their cash boxes.
Adrian Treleven was jailed for 14 years and Remelle Stewart was sentenced to four years detention at Birmingham Crown Court.
Treleven, 26, of Bailey Court, Green Street, Stourbridge and Stewart, 18, of Church Vale, Handsworth Wood, had both previously admitted conspiracy to rob.
Treleven had also pleaded guilty to dangerous driving and driving while disqualified.
Abigail Nixon, prosecuting at Birmingham Crown Court, said: “The prosecution case is that these were three professionally planned attempts to carry out cash in transit robberies targeting high value goods.
“On the March 10 offence there was £14,000 in the cash box.”
She said there were likely to have been similar amounts involved in the other two offences.
“They used stolen untraceable vehicles bearing false plates. Violence was used on each attempt with the violence increasing in gravity.
“Stewart was the get-away driver and Treleven picked him up before each one.”
On February 11 last year a security guard was returning to his van after collecting cash from TK Max in Walsall retail park when he was pushed to the ground by Treleven.
The guard though “bravely” refused to let go while a member of the public intervened and pulled the defendant off.
Treleven then ran to a car being driven by Stewart which made off.
Thirteen days later the pair tried again, this time targeting a security guard with G4S who had been to a Toby Carvery in Chester Road, Sutton Coldfield.
Treleven, who was wearing a balaclava, took a swing at the guard who fell to the floor.
However, the guard fought back at the defendant who was telling him to drop his cash box.
“Treleven then ran to the driver’s side of the car and told Stewart to ‘run him over.” said Miss Nixon.
“Stewart then drove at the victim who managed to jump out of the way and caused him to strike against his van.
“He was terrified they were going to kill him and he had never been so scared,” Miss Nixon added.
The final robbery bid was on March 10 at a Co-op store in Cannock after the defendant had made two “dry runs.”
On this occasion the guard was again approached from behind with Treleven trying to hit him.
The defendant then produced the machete and during the incident suffered a cut to his arm from the blade before the pair fled.
Two days later Treleven was spotted by police in a Nissan in Sparkbrook and tried to get away.
He drove at twice the speed limit, on one occasion mounted the pavement and caused other vehicles to take swerve to avoid a collision.
The defendant struck another car before abandoning the Nissan and tried to escape on foot but was arrested.
Police found a saw and a drill in the vehicle and the machete at his home.
In passing sentence Judge Dean Kershaw said: “You were both targeting large amounts of money, cash in transit robberies.
“It was planned and it was well thought through. You wore disguises.”
And referring to the incident with the machete he said: “You cut that gentleman’s arm. It would have been so much worse.”
Graham Henson, for Treleven, said: “He has not got a history of violent crime. He is still young and went into a different league but failed abysmally.”
While Tarlowchan Dubb, for Stewart, said: “He was recruited by another as a get-away driver. He has learning difficulties and autism. He was intimidated and exploited by the other person.
“He did not even know whether he would have benefited from these offences.”