Paige Dulson suffered a blackout the next day.
Four days later another woman was attacked by a man with a hammer who made similar demands in the Brookside area of Telford.
Miss Katie Fox, prosecuting, said: “The crown says that in January this year this defendant was involved in two separate incidents of violence. Both involved requests for drugs and money.
“Both involved women. Both involved the use of a hammer. In both cases the women knew this defendant."
Miss Fox told the jury at Shrewsbury Crown Court during the first attack on January 20 Miss Dulson was at home with friends and her son.
She said at about 10pm there was a knock at the door. Two men wearing face coverings pushed in asking ‘where the money was’.
As one spoke Paige Dulson recognised the voice, but could not place it at the time. That man carried a hammer.
“He than used the hammer to hit her in the mouth and she also felt a blow to the back of her head.”
The second alleged attack happened on January 24 while victim Terri Meredith and some friends were walking in the Brookside area.
Miss Fox said they were approached by a group of males including the defendant who banged her head against the wall and repeatedly struck her with a hammer, resulting in a suspected fractured eye socket.
Christopher Thomas, 53, of Beaconsfield, Brookside, Telford, denies two counts of attempted robbery and one count of possession of an offensive weapon in a public place, namely a hammer.
The trial continues.