Caladenia woolcockiorum is a terrestrial, perennial, deciduous, herb with an underground tuber and a single hairy, dull green leaf, 60–150 mm long, 10–13 mm wide which has irregular reddish blotches.

[2][3][4] Caladenia woolcockiorum was first described in 1998 by David Jones from a specimen collected in the Flinders Ranges and the description was published in Australian Orchid Research.

[1] The specific epithet (woolcockiorum) honours Collin and Dorothy Woolcock for their assistance to Jones.

[3] Woolcock's spider orchid only occurs in the Mount Remarkable National Park where it mostly grows under shrubs on rocky slopes and on ledges in forest.

The most serious threat is weed invasion but grazing by rabbits and sheep, track maintenance and altered fire regimes also threaten the species.