The incident happened when a black VW Golf was travelling along the Dearne Valley Parkway in the direction of Bridwell when it was in collision with a white Ford Ranger close to the roundabout with Roebuck Hill near to Jump.
The Golf overturned and collided with a lamppost before landing on a grass verge at the side of carriageway.
A 59-year-old man driving the Golf suffered serious injuries and was taken to hospital. The 24-year-old driver and 22-year-old passenger, both men, in the Ranger also sustained injuries.
Police are now appealing for witnesses to the incident, which happened on Saturday, March 4, at about 6.50pm, to come forward.
A spokesperson for the force said: "Were you in the area at the time? Did you witness the collision? If you have any information, please call police on 101, quoting incident number 1037 of 4 March 2017."