The coupling of propagating surface plasmon waves and localized plasmon oscillations in nanostructures is an essential phenomenon determining electromagnetic field enhancement on the nanoscale. Here, we use our recently developed ultrafast photoemission near-field probing technique to investigate the fundamental question of plasmon–plasmon coupling and its effect on large field enhancement factors. By measuring and analyzing plasmon field enhancement values at different nanostructured surfaces, we can separate the contributions from propagating and localized plasmons. When resonance conditions are met, a significant field enhancement factor can be attributed to the generation of localized plasmons on surface nanostructures, acting as dipole sources resonantly driven by the propagating plasmon field. Our plasmon–plasmon coupling results can contribute directly to applications in surface-enhanced Raman scattering (SERS) and the development of plasmonic sensors and nanostructured photocathodes.