The aim of this study was to investigate the aerobic and anaerobic degradation of phenol and its derivatives in aerobic and anaerobic landfills. Phenolic compounds were extracted from leachate samples using the solid phase micro-extraction method. In this study, analysis of the 24 phenolic compounds included in the standard mixture and the change in the concentrations over time of 23 of the 24 compounds found in the calibration mix standard were determined in both aerobic and anaerobic landfill reactors. It can be concluded that faster and complete removal of phenol, chlorophenol, dichlorophenols, and trichlorophenol were achieved in the aerobic landfill while aerobic treatment was less effective on tetrachlorophenol and pentachlorophenol. In the anaerobic landfill, anaerobic reductive dechlorination probably occurred from all the highly chlorinated phenols and resulted in the accumulation of phenol and chlorophenol. The phenol could not be further degraded because the anaerobic methanogenic phase did not start during the 150 days of operation in an anaerobic landfill reactor. Nitrophenols can be degraded rapidly under aerobic conditions. These compounds are degraded to amino groups in the first step and then these amino groups are degraded to methane and CO2 under anaerobic conditions. Although the degradation could not reach the methanogenic phase in anaerobic landfill reactor during the operational period, it is indicated that nitrophenol concentrations decreased in the anaerobic reactor. This is revealed as a result of the formation of the amino groups.