Investigations involving digital forensics typically include file hash matching procedures at one or more steps in the examination. File hash matching is typically done by computing a complete file hash value for each file on a storage device and comparing that to a pre-computed hash list. This work examines how various improvements to the basic technique impact the time required to perform hash matching. Specifically, side-information assisted approaches are evaluated in this work. By utilizing side-information such as file sizes and pre-hashes in addition to the traditional hash values, we find that it is possible to considerably decrease the amount of time required to perform file hash matching. A simulation model is used to evaluate the potential time saving over a range of storage devices and using five different empirically derived file size distribution datasets totaling 36 million file sizes. The results indicate that side-information assisted hashing provides a considerable reduction of the time required, ranging between 5% and 99%, with the majority of cases providing reductions with more than 50%.