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A Fire and Emergency New Zealand spokesman said they were called to the scene at 12:17pm, with one occupant trapped in their vehicle and one of the vehicles involved having rolled onto its roof.
Fire crews from Oamaru, Weston and Kakanui attended the scene.
A St John spokeswoman said the five injured were transferred to Dunedin Hospital in three helicopters, with three patients in serious condition and two in moderate condition.