Force fields belonging to three families were assessed: (i) the second generation General Amber Force Field GAFF-2.11-AM1BCC (hereafter simply referred as GAFF-2.11 ); (ii) the latest version of the Optimized Potentials for Liquid Simulations Force Field (OPLS4 33 ); and (iii) the latest version of each generation of OpenFF force fields (SMIRNOFF99Frosst v1.1 ), OpenFF "Parsley" v1.3.0 39 and the newest release, OpenFF "Sage" v2.0.0. 40 For a pruned dataset of 137,052 molecular conformations of 18,154 small molecules, we compared the structures and energetics of conformers optimized using force fields to those optimized using quantum mechanical methods. This work provides a general understanding of the strengths of different small molecule force fields and identifies areas of improvement for future force field development.