A Yamaha motorbike and red Mini Cooper were involved in a head-on collision on Stopes Road, near Stannington, just before 5.15pm on Tuesday.
A 35-year-old man riding the motorbike ended up trapped between a telegraph pole and wall.
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South Yorkshire Police said the motorcyclist was travelling towards Stannington and the Mini Cooper was heading away from the city suburb at the time of the collision.
It is believed that the motorbike had veered onto the wrong side of the road.
The motorcyclist was taken to the Northern General Hospital by ambulance, where he remains in a serious but stable condition.
The driver of the car involved escaped without serious injury.
Anyone with information should call South Yorkshire Police on 101 and quote incident number 580 of September 17.