This paper presents new state transition matrices that model the relative motion of two spacecraft in arbitrarily eccentric orbits perturbed by J2 and differential drag for three state definitions based on relative orbital elements. These matrices are derived by first performing a Taylor expansion on the equations of relative motion including all considered perturbations and subsequently computing an exact, closed-form solution of the resulting linear differential equations. Both density-model-specific and density-model-free differential drag formulations are included. Density-model-specific formulations require a-priori knowledge of the atmosphere, while density-model-free formulations remove this requirement by augmenting the relative state with a set of parameters which are estimated in flight. The resulting state transition matrices are used to generalize the geometric interpretation of the effects of J2 and differential drag on relative motion in near-circular orbits provided in previous works to arbitrarily eccentric orbits. Additionally, this paper harmonizes current literature by demonstrating that a number of state transition matrices derived by previous authors using various techniques can be found by subjecting the models presented in this paper to more restrictive assumptions. Finally, the presented state transition matrices are validated through comparison with a high-fidelity numerical orbit propagator. It is found that the models including density-model-free differential drag exhibit much better performance than their density-model-specific counterparts. Specifically, these state transition matrices are able to reduce propagation errors by at least an orderof-magnitude when compared to models including only J2 and are able to match or exceed the accuracy of comparable models in literature over a broad range of orbit scenarios.