Eye-witnesses claimed they saw a third man running away from the scene – described as a "bloodbath" – in Bournemouth Road in Chandlers Ford, near Southampton. A man was arrested last night in connection with the attempted robbery.
The Independent Police Complaints Commission (IPCC) is investigating the shootings, which allegedly happened as one of the robbers held a gun to the head of a security guard, after he had been ordered by police to drop his weapon.
Police officers appear to have been closely monitoring the robbers as they targeted the van, which was calling at a branch of HSBC bank to deliver cash.
Hampshire police would not confirm last night that the robbers had been armed, but a spokeswoman for the IPCC said: "A live firearm was recovered from the scene."
Witnesses described hearing several shots, as up to 30 plain clothed officers emerged from a nearby public lavatory and descended on the scene just after 10am.
One man was killed instantly and the second died in hospital, Scotland Yard confirmed.
One witness, Melanie Chase, who lives above the bank, said: "I was in the bath when I heard someone shouting 'Get down, Get down' and then I heard three shots. I looked out of the window and saw blood everywhere on the floor. It was horrible."
Another onlooker, Lynn Ward, who works at the Alexander Keen estate agents' next door to the bank, said she also heard the shouts of "get down" after a loud bang, which at first she thought was a traffic accident.
"But when I looked out of the window I saw a security van and two people on the floor with armed police stood over them," she said. " It was chaos. There was lots of shouting and screaming. It was then I realised it must have been gunshots. Chandlers Ford is a rural town and you certainly do not expect this kind of thing to happen."
Employees at the estate agents' rushed out of the back of their offices when they heard the gunshots. "I knew it was the sound of bullets immediately. Everyone just ran to get as far away as possible," one said. "The police must have been tipped off. One customer told us they saw police officers running out of the public toilets just near to the bank and then they heard the shots."
Jamie Owens, 16, who lives above the bank, said he was woken by gunfire and saw two men, one of mixed race and the other white, lying in the road as a helicopter circled overhead.
He said his neighbours told him they saw a third man escaping from the scene. They told him that the robbers, demanding money, put a gun to one of the guards' heads and at this point they were shot, according to the witnesses. There were reports last night that police marksmen may have been waiting on top of buildings nearby.
Scotland Yard said officers from its Flying Squad had been carrying out a "pro-active operation" with Hampshire Police.
"The object of the operation was to prevent and apprehend those believed to be involved in an attempted armed robbery of a premises in Chandler's Ford," it said in a statement
Mr Owens said: "I heard two gunshots ... I thought it was just a car backfiring, then I heard a woman screaming, heard a lot of commotion and I saw the two men lying on the floor. Their clothes were stripped off them with tape on their chests as they tried to resuscitate them, but one wasn't moving at all.
"There were 25 to 30 undercover police officers with Metropolitan Police across their caps with big machine guns. They were shouting at people that they had to go home, they must leave the area. I saw a lot of police around. I saw a helicopter landing in the street."
Despite last night's arrest, which was confirmed by Scotland Yard, police had earlier refused to confirm the claims that a third man had fled the scene, but witnesses said that police near the scene, who went into the estate agents' to discuss the incident, had said as much.
A spokesman for HSBC confirmed no customers or staff were hurt, and said: "We are obviously very grateful because this violent incident appears to have had the potential to have been much worse."
Hampshire police said that no officers or bystanders had been injured during the shootings.
The IPCC said in a statement: "The IPCC investigators are attending the scene to gather evidence for the inquiry which will look at the circumstances of the shooting as well as the planning and implementation of the operation."
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