Police are appealing for witnesses after it occurred at around 11.30am on Rochdale Road, near to the junction of Pye Nest Road.
It involved a silver Volkwagen Golf and skip truck.
The driver of the Golf, an 82-year-old man, and the front seat passenger of the same car, a 79-year-old man, were taken to Huddersfield Royal Infirmary.
The passenger sustained serious injuries, whilst the driver sustained minor injuries.
The driver of the skip truck was not injured.
Road closures were in place in to the early evening for recovery and investigation works to take place.
Officers are appealing to anyone who have been in the area and saw either vehicle in the time before the collision, or who witnessed the it to come forward.
Information can be passed to the Western Safer Roads and Neighbourhood Support Team via 101 quoting 13170596721.