This paper presents the fabrication of metallic micro-mushroom re-entrant structures and the characterization of their hydrophobicity and oleophobicity. Five different microstructure geometries are introduced, with typical feature sizes in the range of 10–100 μm. These microstructures are realized in steel, and are fabricated over the cm-scale using micro electrical discharge machining (mEDM). The liquid repellency of these surfaces is characterized using droplets of either water (surface energy γlg = 72.4 mN m−1), RL-68H oil (γlg = 28.6 mN m−1), or Isopropanol (IPA) (γlg = 21.7 mN m−1). The water droplets form nearly perfect spheres, with contact angles in the range 146–162°, and contact angle hysteresis of 19–35°. The oil droplet contact angles are in the range 106–152° and the IPA contact angles are in the range 75–123°. Strong re-entrant features and close spacing are necessary to support a fully non-wetting state for use with oil and IPA. Water forms the highest contact angles with narrow, post-like, and widely spaced micro-mushroom geometries.