Inverted-headgroup (choline-phosphate) lipids are synthetic lipids that are not found in nature and are used as model systems to understand the role of headgroup dipole orientation. Recently, studies revealed that the net orientation of interfacial water strongly depends on the headgroup electrostatics, i.e., the charges and dipole generated by the phosphate and the choline groups. In order to characterize interfacial H-bond dynamics, we measured two-dimensional infrared spectra of the ester carbonyl band and performed molecular dynamics simulations in fully hydrated 1,2-dioleoyl-sn-glycero-3-phosphocholine and 2-((2,3-bis(oleoyloxy)propyl)-dimethyl-ammonio)ethyl ethyl phosphate (DOCPe) lipid bilayers. The experiments and simulations suggest that the reverse dipole generated by the inverted-headgroup in DOCPe does not affect the carbonyl H-bond populations or the interfacial water H-bond dynamics. However, while phosphate-associated waters in both lipids appear to show a similar H-bond structure, carbonyl-associated waters are characterized by a slightly disrupted H-bond structure in the DOCPe bilayer, especially within the second hydration shell. Our findings show that changes in net water orientation perturb the water H-bonds at the linker region between the headgroup and the lipid tail, although this perturbation is weak.