We demonstrate how distinct surface plasmon resonance modes on opposite sides of a metal-coated grating can be coupled across the metal film. This coupling occurs by matching the resonance conditions on each side of the grating by tuning the refractive index directly adjacent to the metal film. In the first example, we deposited a high refractive index layer of tin oxide on top of the grating to red-shift the front side surface plasmon until it coupled with the backside surface plasmon across a semitransparent ∼45 nm thin silver grating. By shifting the resonance condition of the nearby surface plasmon, this high refractive index coating creates an effective matching of wave vectors across the metal film, allowing them to couple and enhance the optical response. A massive increase in the magnitude of enhanced transmission is observed, increasing from a 6-fold transmission enhancement through a bare silver grating to a near 100-fold enhancement after deposition of a tin oxide layer of appropriate thickness (∼310 nm). This optical transmission enhancement is then probed through computational modeling and by experiments with liquids of various refractive index values. The matched system shows an increased amplitude sensitivity with respect to refractive index changes and a waveguide like behavior within the tin oxide film. As an alternative configuration, we also demonstrate coupling the front and back-side plasmon modes by using a lower refractive index substrate in order to blue-shift the back-side surface plasmon. Coupling between the two plasmon modes is then demonstrated by introducing aqueous solutions of various refractive index values. Under the proper conditions, this matched system also shows a substantial enhancement in transmission. This technique of wave vector matching provides a route to substantially increasing the plasmon enhanced optical transmission through metal gratings, which has potential application in improved plasmonic sensing, spectroscopy, and plasmon-based optical devices.