Two case studies of oil spills that demonstrate the changing distribution patterns resulting from long-term anaerobic microbial degradation were presented. These spills were the 1979 crude-oil spill in Bemidji, MN, and a chronic diesel-fuel spillage from 1953-1991 at Mandan, ND. The alkylcyclohexanes in both spilled oil products were affected by similar biodegradative processes in which the compounds underwent a consistent pattern of loss from the high molecular weight end of the homolog distribution. Degradation resulted in a measurable increase in the concentrations of the homologs in the lower molecular weight range, a gradual lowering in carbon number of the homolog maximum, and a gradual decrease of the total homolog range from the high molecular weight end. The Mandan diesel fuel spill showed that the progressive enhancement of the low-molecular-mass n-alkane and n-alkylcyclohexane homologs reflected an absolute increase in their concentrations as the high-molecular-mass homologs were diminishing. These degradation patterns were different from those observed in aerobic or physically weathered systems, where loss of n-alkenes and other aliphatic homologs occurred from the low molecular weight end of the distributions. Spilled diesel and other mid-cut refinery fuels were defined by the range and distribution of the n-alkylcyclohexanes. If the biodegradation has progressed well into or beyond n-alkane loss and to the stage of low-molecular-mass n-alkylcyclohexane enhancement and high-molecular-mass loss, the hydrocarbon pattern could be erroneously attributed to other lower-range middle distillate fuels or admixtures of fuels. This is an abstract presented at the 25th Arctic and Marine OilSpill Program Technical Seminar (Calgary, Alberta, 6/11-13/2002).