A magnetic stir bar with a polydimethylsiloxane coating was used to absorb 2,4,6-trichloroanisole, 2,3,4,5-tetrachloroanisole, pentachloroanisole and their respective phenols from synthetic and real wine samples. The stir bar sorptive extraction method was optimised to obtain the best extraction conditions in terms of temperature, time, pH and NaCl addition. The stir bar was desorbed in a thermal desorption system coupled to a gas chromatograph-mass spectrometer. The method proposed showed good linearity over the concentration range tested and correlation coefficients ranged from 0.96 to 0.99 for all the analytes. The reproducibility and repeatability of the method was estimated between 1.29 and 4.02%. With no a pre-concentration step and with a much reduced analysis time, all the analyzed compounds showed detection and quantification limits that were lower than those observed with other methods found in the bibliography. Except for pentachlorophenol due to its poor absorptivity in polydimethysiloxane, in red wines, LOD ranged between 7.56 and 61.56 pg/l, and LOQ ranged between 17.21 and 205.11 pg/l; while in white wines, the LOD ranged between 5.82 and 30.50 pg/l and LOQ ranged between 19.41 and 101.61 pg/l. These concentrations were always lower than their respective olfactory thresholds values.