In this article, we report metal-enhanced singlet oxygen generation (ME(1)O2). We demonstrate a direct relationship between the singlet oxygen yield of a common photosensitizer (Rose Bengal) and the theoretical electric field enhancement or enhanced absorption of the photosensitizer in proximity to metallic nanoparticles. Using a series of photosensitizers, sandwiched between silver island films (SiFs), we report that the extent of singlet oxygen enhancement is inversely proportional to the free space singlet oxygen quantum yield. By modifying plasmon coupling parameters, such as nanoparticle size and shape, fluorophore/particle distance, and the excitation wavelength of the coupling photosensitizer, we can readily tune singlet oxygen yields for applications in singlet oxygen-based clinical therapy.