Thomas Smith had already followed another female shortly before he turned his attention on the 66-year-old widow and pounced with a weapon, believed to be a heavy object wrapped in cloth.
Sinister CCTV shows Smith running up behind the victim with the weapon in his hand just before he struck.
Newcastle Crown Court heard as the victim struggled to protect herself, Smith hit her head with the object, twice, leaving her bleeding from two deep cuts and in need of hospital treatment.
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Smith, 63, has a previous conviction from the 1990s for abducting a 13-year-old child from the street in Washington and indecently assaulting her as she cried for help before she was rescued by two passing strangers.
Judge Christopher Prince said the robbery, which happened in Houghton, in April 2019, had "striking similarities" to the attack more than 20 years earlier.
Judge Prince said: "Both involve following and targeting comparatively vulnerable females."
The judge said Smith has a "willingness to target vulnerable females" and is a dangerous offender so imposed an additional four year licence period, on top of the ten-year jail term, to protect the public.
Judge Prince said Smith poses a "high risk to vulnerable females".
Prosecutor Joe Culley told the court the widow had been walking along a footpath near a medical centre in Houghton and had her handbag in her hand whenSmith approached from behind.
Mr Culley added: "She stepped aside to let the person pass but he grabbed her handbag.
"She resisted and he hit her to the top of the head with an object he had in his hand, causing her to feel pain.
"She felt blood coming from her head and he pulled her bag a second time then struck her again, this time behind the left ear.
"She feared he would continue to hit her so she let go."
The court heard Smith ran off with the bag, which itself was precious to the victim contained sentimental items including photographs of her late husband, which she never got back.
She said she was left feeling "vulnerable and unsafe" and still feels the affects of that day.
Mr Culley added: "The prosecution case is he followed her before robbing her.
Before robbing her he appeared to have been following another female in a similar way.
"He was seen to be carrying an object in his left hand."
Smith, of Edward Street, Hetton, was identified by a police officer from CCTV but denied robbery and was convicted by a jury after a trial.