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At 2.20pm on Friday 15 May a white Mini was involved in a collision with a blue Ford Transit while travelling along the A171 eastbound carriageway.
The driver of the Mini was taken to James Cook University Hospital for treatment, and the driver and passenger of the Ford Transit were treated at the scene.
Officers investigating the collision are appealing to anyone who may have witnessed it take place or have information to get in touch.
They are also appealing for any dash cam footage to be submitted.
You can report information and footage to Cleveland Police by contacting 101 or visiting the website quoting reference number 092136.