The driver of the red Ford KA received serious head injuries when the vehicle overturned on the approach to Battlefield roundabout junction of the A53/A49.
He was taken to the Royal Shrewsbury Hospital before being transferred to the University Hospital of North Staffordshire in Stoke.
A front seat passenger suffered cuts and bruises but was not believed seriously injured.
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A West Mercia Police spokesperson said: “The vehicle was travelling along the A53 from Market Drayton towards Shrewsbury at around 9.45pm on Tuesday when it lost control on the approach to the roundabout.
“Anyone who saw what happened is asked to contact Shrewsbury police station on 101.”
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