Enhancing the output power of triboelectric nanogenerators (TENGs) requires the creation of micro or nano-features on polymeric triboelectric surfaces to increase the TENGs’ effective contact area and, therefore, output power. We deploy a novel bench-top fabrication method called dynamic Scanning Probe Lithography (d-SPL) to fabricate massive arrays of uniform 1 cm long and 2.5 µm wide nano-features comprising a 600 nm deep groove (NG) and a 600 nm high triangular prism (NTP). The method creates both features simultaneously in the polymeric surface, thereby doubling the structured surface area. Six thousand pairs of NGs and NTPs were patterned on a 6×5 cm2 PMMA substrate. It was then used as a mold to structure the surface of a 200 µm thick Polydimethylsiloxane (PDMS) layer. We show that the output power of the nano-structured TENG is significantly more than that of a TENG using flat PDMS films, at 12.2 mW compared to 2.2 mW, under the same operating conditions (a base acceleration amplitude of 0.8 g).