Frequency-dependence and magnitude of second harmonic generation (SHG) from ~4 × 105 nm2 molybdenum disulfide (MoS2) monolayers was examined in presence of single 150 nm plasmonic gold@silica shell@core nanoantenna monomer and dimers. Quantitative agreement between discrete dipole approximation-calculated fields and measured SHG enhancements was found. SHG from MoS2 was enhanced up to 1.88 × upon deposition of a plasmonic nanoantenna-dimer with 170 nm gap, reaching maximal normalized SHG conversion efficiency of 0.0250%/W. Pump losses attributable to plasmonic damping, e.g., scattering and/or hot-electron injection into MoS2, were apparent. Linear and nonlinear optical activity of MoS2 and nanoantenna controls were compared with literature values.