We present a case study about inkjet printing as a tool for molecular patterning of silicon oxide surfaces with hydrophobic functionality, mediated by n-octadecyltrichlorosilane (OTS) molecules. In contrast to state-of-the-art techniques such as micro contact printing or chemical immersion with subsequent lithography processes, piezo drop-on-demand inkjet printing does not depend on physical masters, which allows an effective direct-write patterning of rigid or flexible substrates and enables short run-lengths of the individual pattern. In this paper, we used mesithylene-based OTS inks, jetted them in droplets of 10 pL on a silicon oxide surface, evaluated the water contact angle of the patterned areas and fitted the results with Cassie's law. For inks of 2.0 mM OTS concentration, we found that effective area coverages of 38% can be obtained. Our results hence show that contact times of the order of hundred milliseconds are sufficient to form a pattern of regions with OTS molecules adsorbed to the surface, representing at least a fragmented, inhomogeneous self-assembled OTS monolayer (OTS-SAM).