Video footage has captured the moment an elderly woman tried to fight off a mugger with crutches as he grabbed her handbag.
Jason Sheldon, 31, rode up to the 77-year-old victim on his bike in Newark, Nottinghamshire on 28 February just after 5.40pm, Nottinghamshire Police said.
He then grabbed the strap of the unnamed victim's handbag and the force pulled her off balance.
She dropped one of her crutches but managed to stay on her feet, police added.
Footage of the incident shows the victim trying to fend off Shelton by hitting him with her crutch, which she was using following a knee replacement.
As he retreated on his bike, the woman also shouted at him to give her bag back, police said.
Sheldon, from Newark, managed to flee with the bag which contained house keys, a rain jacket and a small bag containing loose change.
Just two minutes later he targeted another victim - a 52-year-old man who had just used a cash machine and was walking back to his home.
As the man was unlocking his front door, Sheldon hit him on the side of the head, knocking him to the floor.
He then repeatedly punched him and demanded the cash as the victim was left lying on his side.
The man managed to push the cash underneath the front door so that Sheldon could not get to it.
The 31-year-old kept threatening the victim before riding off, leaving the man with a concussion, a black eye and lumps to his head.
Sheldon was later arrested and charged and convicted of charged of robbery and attempted robbery following a two-day trial at Nottingham Crown Court.
He was sentenced on Friday to six years in prison at Nottingham Crown Court.
Detective Constable John Wilson of Nottinghamshire Police, said: "To attack an elderly and vulnerable woman on crutches in this way is absolutely despicable.
"When the incident was reported and we saw the video footage we were shocked at how someone could do something like this and we were determined to bring him to justice."
He added: "I'd like to commend the bravery shown by both victims, not only during these appalling crimes but also during our investigations into them.
"These were callous attacks and Sheldon showed a complete disregard to the victims' welfare. It's fortunate that they didn't suffer even more serious injuries.
"I hope this conviction and sentencing will serve as a warning to others."
Watch: Thugs lay in wait for wheelchair-bound pensioner, 69, who was beaten to death