Cunninghamhead is a hamlet on the Annick Water in the Parish of Dreghorn, North Ayrshire, Scotland. The area was part of the old Cunninghamhead estate, and once contained several watermills.

The Annick Water is the largest tributary of the River Irvine. The river runs from Long Loch, just inside East Renfrewshire, in a generally south-western direction through North Ayrshire and East Ayrshire, to confluence with its parent river at Irvine, North Ayrshire on the west coast of Scotland. The name may derive from the Gaelic for 'overflowing' and Strathannick is very much prone to flooding as recorded by SEPA.