The stereoselective dissipation of flutriafol and tebuconazole in grape had been studied. A simple and sensitive method for determination of flutriafol and tebuconazole enantiomers in grape was developed by high-performance liquid chromatography on a cellulose tris(3-chloro-4-methylphenylcarbamate) column. The limits of quantification for flutriafol and tebuconazole in grape were 0.033 and 0.043 mg kg(-1), respectively. The dissipations of flutriafol and tebuconazole stereoisomers in grape followed first-order kinetics (R (2) > 0.93). The stereoisomers of flutriafol and tebuconazole were enantioselectively degraded in grape, and tebuconazole was more enantioselective than flutriafol. The half-life of (-)-tebuconazole was 5.2 days and shorter than (+)-tebuconazole with half-life of 6.4 days. The (-)-flutriafol was also preferentially degraded in grape, the half-lives of which were 6.59 and 6.98 days for (-) and (+)-flutriafol, respectively. The enantiomeric ratio value of the two fungicides was nearly 1.0 at the 1st day and increased to 1.143 for flutriafol and 2.015 for tebuconazole at the 28th day. The stereoselective dissipations could provide a reference to fully evaluate the risks of two important chiral triazole fungicides.