Organochlorine pesticides (OCPs) and phthalates are amongst the most emphasized man-made environmental contaminants, due to their prevalence, persistence and potential to induce adverse effects in organisms. In addition to prevailing industrial and domestic activities, their presence in the environment is exacerbated by leaching from associated materials, run-off and emissions. The Loskop Dam in the Mpumalanga Province, South Africa, is located on the Olifants River, which flows through a hub of industrial and agricultural activities. Research aimed at monitoring the levels of OCPs and phthalate contamination in South Africa, particularly in the Olifants catchment, has been limited and is restricted to short-term monitoring. In this study, the spatial and temporal variations of 21 OCPs and 7 phthalates in water and sediments from Loskop Dam were evaluated over a 3-year period (2015–2017). Annual average OCP levels ranged from 0.013±0.006 to 0.36±0.13 μg/L in water and from below the limit of detection to 2.4±1.2 µg/kg in sediments. Phthalates were present at average concentrations ranging from 0.023±0.041 to 2.1±1.5 μg/L and 20±0.63 to 55±6.9 µg/kg in water and sediments, respectively. The levels of OCPs and phthalates were greatest in autumn, attributed to higher input sources and concentration effects due to lower water levels. Phthalates were present at greater quantities at the inlet, while OCP accumulation was observed at the upper reaches of the dam. This may be an indication of the differences in input sources and translocation of these compounds, related to the topography of the dam and variability in water flow rates. These findings are important in highlighting the environmental and health concerns that may arise in the Olifants catchment area. After considering the outcomes of this study, we propose the implementation of regular and stringent monitoring strategies, which include surveys of OCPs and phthalates for Loskop Dam and similar water systems globally.