Scottish Fire and Rescue Service (SFRS) crews were sent to Lanark Road in Crossford shortly before 6pm after receiving reports of the collision.
Crews from Lanark and Carluke community fire stations along with a heavy rescue vehicle from Easterhouse arrived to find one person had left the van and was already in the care of the Scottish Ambulance Service, whose team were also assessing the condition of the trapped driver before work began to release him.
Firefighters used hydraulic cutting equipment to rescue the motorist, working side-by-side with paramedics while police officers closed the road to ensure the safety of everyone at the scene.
Ambulances took the two men to Wishaw General Hospital.
No-one was in the house at the time of the incident.