The crash happened shortly after 3pm yesterday on the A658 at Follifoot, at the junction with Haggs Road, and involved a white Mercedes-Benz C220, a grey Mini and a silver Porsche.
The driver of the Mini a man, from Newcastle, is in a serious but stable condition at Leeds General Infirmary.
The road was closed until 9pm yesterday as emergency services worked at the scene and to allow a police examination.
Police are appealing for witnesses.
Anyone who saw the crash, or any of the vehicles before the collision, are urged to call North Yorkshire Police on 101, select option 2, and ask for Pete Stringer or email [email protected], quoting reference 12180224633.