A total of 171 oils and 11 core plugs were collected from the Woodford Shale, the Mississippian Group, and the Springer Group reservoirs of the Anadarko Basin, Oklahoma. Geochemical variations in the oils led to the identification of four organic facies that could be mapped across the Sooner Trend Anadarko Basin, Canadian, and Kingfisher Counties (STACK) and South-Central Oklahoma Oil Province (SCOOP) plays. Oils produced from Woodford and Mississippian Group reservoirs were generated from three organic facies across the large-scale Woodford depositional system. The facies ranged from sediment-starved restricted marine in the Northwest Extension of STACK, shallow open marine in the core of STACK, and clay-rich open marine in SCOOP. In contrast, SCOOP oils produced from the Springer Group reservoirs were generated from a separate organic facies deposited in a clay-rich open marine depositional environment, probably the Caney or Goddard Shales. The vitrinite reflectance equivalent calculated from the methylphenanthrene index for oil samples ranged between 0.74% and 1.43%. A narrow zone of deep, volatile oil production in STACK West, associated with H2S production, contained relatively high concentrations of organic sulfur components, suggesting that deep fluids, possibly impacted by thermochemical sulfate reduction, may have migrated updip and mixed with lower-maturity oils. It would appear unlikely that Mississippian source rocks in STACK have made any serious contribution to the STACK oils. The outcome of the study confirms that most of the oils are produced from a Woodford source and have undergone short-distance migration to the reservoirs. This is manifested by positive relationships between numerous maturity parameters measured for the oils and the corresponding vitrinite reflectance equivalent values measured in the vicinity of production.