The collision happened at 7.10pm on Tudworth Road, Thorne, and involved a blue Peugeot 206 and a blue Skoda Rapid.
The second car is then believed to have been involved in a further collision with a black Vauxhall Zafira.
An 18-year-old man, who was driving the Peugeot, was rushed to hospital with life-threatening injuries and police said he remains in a critical condition today.
Three women, and a man, travelling in the Skoda and an 18-year-old woman passenger in the Peugeot all also suffered minor injuries.
Anyone with information is asked to call 101 or email [email protected] quoting incident number 983 of 20 December 2016.