The Woodford-Mississippian "Commingled Production" is a prolific unconventional hydrocarbon play in Oklahoma, USA. The tight reservoirs feature variations in produced fluid chemistry usually explained by different possible source rocks. Such chemical variations are regularly obtained from bulk, molecular, and isotopic characteristics. In this study, we present a new geochemical investigation of gasoline range hydrocarbons, biomarkers, and diamondoids in oils from Mississippian carbonate and Woodford Shale. A set of oil/condensate samples were examined using high-performance gas chromatography and mass spectrometry. The result of the condensates from the Anadarko Basin shows a distinct geochemical fingerprint reflected in light hydrocarbon characterized by heptane star diagrams, convinced by biomarker characteristics and diamantane isomeric distributions. Two possible source rocks were identified, the Woodford Shale and Mississippian mudrocks, with a variable degree of mixing. Thermal maturity based on light hydrocarbon parameters indicates that condensates from the Anadarko Basin are of the highest maturity, followed by "Old" Woodford-sourced oils and central Oklahoma tight oils. These geochemical parameters shed light on petroleum migration within Devonian-Mississippian petroleum systems and mitigate geological risk in exploring and developing petroleum reservoirs.