A supported lipid bilayer (SLB) is now an indispensable tool to analyze the dynamical properties of biomembranes. However, the effect of a solid support on the leaflet-specific lipid dynamics in a SLB remains elusive, which hampers the further application of the SLB as a model biomembrane. Here, we performed the leaflet-specific lipid diffusion analysis by means of two-dimensional fluorescence lifetime correlation spectroscopy to elucidate the effect of the electrostatic interaction between lipid headgroups and a glass surface on the lipid diffusion in each leaflet of the SLB. The results clearly showed the correlation between the strength of the electrostatic interaction and the lipid diffusion in the proximal leaflet of the SLB facing a glass surface. In particular, the electrostatic attraction between the cationic lipids and a negatively charged glass surface enhanced the lipid diffusion in the proximal leaflet of the SLB, providing important implications for the lipid dynamics not only in the SLB but also in biomembranes.