Chiral honeycombs are a class of auxetic metamaterials which are characterised by a lack of plane symmetry. Besides the traditional chiral honeycombs based on regular monohedral tessellations such as the hexachiral and tetrachiral honeycombs, a vast range of auxetic chiral metamaterials may be produced through the ‘chiralisation’ of Euclidean tessellations made from polyhedral tilings and/or irregular monohedral polygons. In this work, we show for the first time, how the direction of the geometric chiral transformation, i.e. clockwise vs anti-clockwise chiralisation, has an influence on the mechanical properties and deformation modes of the resultant chiral metamaterial systems. This influence, which is a result of the intrinsic absence of axial symmetry in the original base tessellation, can lead to the production of two unique and distinct chiral metamaterial configurations with completely different mechanical properties originating from a single base tessellation. In this work we demonstrate and quantify, through a wide range of numerical simulations and experimental tests on additively-manufactured prototypes, the effect of the direction of chiralisation on two tessellations: a Florent pentagonal system with hexagonal rotational symmetry and a hexagonal monohedral tessellation with trigonal rotational symmetry. The results obtained show that the clockwise and anti-clockwise chiral structures exhibit significantly different mechanical properties and deformation modes, highlighting the increased versatility of this relatively novel class of chiral metamaterials.