Chiral liquid chromatography-tandem mass spectrometry (HPLC/MS/MS) was used to measure pharmaceuticals in surface and wastewaters. Analytes measured were chiral non-steroidal anti-inflammatory drugs (NSAIDs) ibuprofen, naproxen, fenoprofen, ketoprofen; β-blockers metoprolol, atenolol and propranolol; and selective serotonin re-uptake inhibitor fluoxetine. Achiral drugs measured were NSAIDs diclofenac and indomethacin; lipid regulators clofibric acid and gemfibrozil; and stimulant caffeine. Water samples were concentrated by solid phase extraction and target analytes separated using Chiralpak AD-RH and Chirobiotic V columns. Recoveries (60 to 108%), linearity (0.9739 to 0.9969) and limits of detection (LOD) (0.01 to 39 ng/L) were compared to previous measurements in environmental waters. Stereoisomers of chiral targets were separated (resolution factors between 0.6 and 0.9) and enantiomer fractions (EFs) were determined. Analytes were detected in most environmental samples. Non-racemic EFs were seen in WWTP effluent samples and in Lac la Biche WWTP influents. No chiral targets were seen in the surface water samples.