Using a scanning tunneling microscope-based break-junction technique, we assessed the conductance of single-molecule junctions formed with three distinct molecular wires, each featuring a cyclic five-membered ring: furan, cyclopentanone or cyclopentadiene. We found that the conductance of these three wires correlates with their aromaticity; the non-aromatic cyclopentadienone derivative exhibits the highest conductance, while the most aromatic furan in this series displays the lowest conductance. Additionally, the lower HOMO-LUMO gap of anti-aromatic compounds may also contribute to this effect. This discovery aids in understanding the influence of molecular structure on conductive properties and provides crucial insights for the design and optimization of molecular electronic devices.