This paper addresses the challenging scheduling of crude oil operations (SCOO) problem, characterized by the intricate sequencing of activities involving discrete events and continuous variables. Given the NP-Hard nature of scheduling problems due to their combinatorial complexity, this study employs a data-driven optimization approach. Initially, historical operational data relevant to the SCOO are scrutinized; however, due to data limitations, small-scale instances are solved using a mathematical programming model to generate data. Subsequently, operational solution data are processed using the Apriori algorithm, a renowned data mining technique. The insights gained are translated into heuristic rules, laying the groundwork for a novel data-driven heuristic algorithm tailored for the SCOO problem. This algorithm is then applied to a 45-day scheduling scenario, demonstrating the efficacy of the proposed approach.