Milkman Ian Sears crashed into a woman's car with his float - and later did the same to her mother's car.
Hairdresser Jeanette Leafesaid: "It was an incredible coincidence."
She said the Unigate Dairy Crest milkman reversed his 15mph electric float into her new £14,000 Mini Cooper, causing nearly £4,000 damage.
Two weeks later he backed into a £5,000 Vauxhall Vectra owned by her mother, Maureen Leafe. The repair bill is expected to be several thousand pounds.
Miss Leafe, 35, of Wantage, said: "I had had my lovely silver Mini Cooper for only four weeks - it has a personal number plate."
Miss Leafe was in Stirling Close, Wantage, on a shopping errand for her grandmother when she reversed to let someone cross the road.
Miss Leafe said: "I was stationary when there was a bang behind me. I saw a milk float jammed in the back of my car. The milkman was very apologetic and told me he was in a blind spot."
Two weeks later, Mrs Leafe, 59, an auxiliary nurse, also of Wantage, parked her car in Maria Crescent.
She said: "I moved my car to where I thought the milkman would see the vehicle. But minutes later, I answered a knock on the door and there was the milkman.
"He asked if I owned the car outside because he had just reversed into it and smashed the bonnet and lights. I couldn't believe it."
Mr Sears, 53, of Laburnum Grove, Didcot, has been given a warning by his manager at the dairy's Abingdon depot.
A Dairy Crest spokesman said: "Appropriate action has been taken."
Mr Sears has been told by police he may face charges for careless driving.
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