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In the present work, the liquid−liquid phase equilibrium data for the glycerol−methanol−methyl oleate and glycerol−monoolein−methyl oleate ternary systems were determined experimentally and compared with predictions of the UNIFAC and UNIFAC-Dortmund models. Liquid two-phase multicomponent systems consisting mainly of these chemical species are found in some industrially important transesterification reactions. For the glycerol−methanol−methyl oleate ternary system at 60 °C, the predictions of UNIFAC and UNIFAC-Dortmund are in good agreement with the experimental results. For the ternary glycerol−monoolein−methyl oleate system at 135 °C, the predictions of UNIFAC and UNIFAC-Dortmund deviate significantly from the experimental data and are only qualitatively correct. The reliability of the experimental data was determined through Othmer−Tobias plots.