Phenolic compounds occur in a variety of plants and can be used as model compounds for investigating the fate of organic wastewater, lignin, or soil organic matter in the environment. The aim of this study was to better understand and differentiate mechanisms associated with photo- and biodegradation of tyrosol, vanillin, vanillic acid, and coumaric acid in soil. In a 29 d incubation experiment, soil spiked with these phenolic compounds was either subjected to UV irradiation under sterile conditions or to the native soil microbial community in the dark. Changes in the isotopic composition (δ13C) of phenolic compounds were determined by gas chromatography–isotope ratio mass spectrometry and complemented by concentration measurements. Phospholipid-derived fatty acid and ergosterol biomarkers together with soil water repellency measurements provided information on soil microbial and physical properties. Biodegradation followed pseudo-first-order dissipation kinetics, enriched remaining phenolic compounds in 13C, and was associated with increased fungal rather than bacterial biomarkers. Growing mycelia rendered the soil slightly water repellent. High sample variation limited the reliable estimation of apparent kinetic isotope effects (AKIEs) to tyrosol. The AKIE of tyrosol biodegradation was 1.007 ± 0.002. Photooxidation kinetics were of pseudo-zero- or first-order with an AKIE of 1.02 ± 0.01 for tyrosol, suggesting a hydroxyl-radical mediated degradation process. Further research needs to address δ13C variation among sample replicates potentially originating from heterogeneous reaction spaces in soil. Here, nuclear magnetic resonance or nanoscopic imaging could help to better understand the distribution of organic compounds and their transformation in the soil matrix.