Interactions between molecules and at interfaces are vital to many scientific and technological fields. Techniques such as atomic force microscopy (AFM) have been used to measure forces and force gradients associated with interactions between individual molecules as well as interactions between interfaces. A recent alteration of the AFM configuration combined a tipless cantilever with an array of substrate supported tips. Herein, we present a further extension of AFM force measurement capabilities, by chemically patterning both the cantilever and the tip array. In a proof-of-concept experiment a gold-coated cantilever and tip array were patterning with alkylthiolate monolayers, and the interfacial forces were measured for the various combinations. This patterning allows many different interactions to be rapidly measured in situ, under identical conditions, thereby improving reliability and opening the door to combinatorial applications. Future developments are discussed including the means to measure hundreds of different interactions.