A new quantitative method based on static headspace−gas chromatography−ion mobility spectrometry (SHS−GC−IMS) is proposed, which enables the simultaneous quantification of multiple aroma compounds in wine. The method was first evaluated for its stability and the necessity of using internal standards as a quality control measure. The two major hurdles in applying GC-IMS in quantification studies, namely, non-linearity and multiple ion species, were also investigated using the Boltzmann function and generalized additive model (GAM) as potential solutions. Metrics characterizing the model performance, including root mean squared error, bias, limit of detection, limit of quantification, repeatability, reproducibility, and recovery were investigated. Both non-linear fitting methods, Boltzmann function and GAM, were able to return desirable analytical outcomes with an acceptable range of error. Potential pitfalls that would cause inaccurate quantification i.e., effects of ethanol content and competitive ionization, were also discussed. The performance of the SHS-GC-IMS method was subsequently compared against a currently established method, namely, GC-MS, using actual wine samples. These findings provide an initial validation of a GC-IMS-based quantification method, as well as a starting point for further enhancing the analytical scope of GC-IMS.