Energy transfer improvement and energy consumption reduction are getting more crucial in the automotive sector. As one of the essential elements directly influencing energy transfer in the powertrain system, transmission losses have been widely analyzed with both simulation and experimental approaches. For a better characterization of individual losses, this paper investigates and compares most of the available analytical models for further system implementation. Regarding laboratory experiments, an adaptive sampling strategy is presented and analyzed for various operating conditions. Compared to the traditional factorial design, the applied Gaussian Process Regression (GPR) delivers both estimations and their predictive variances in the entire experiment process. Besides, new measurement candidates can be determined with the prior information from GPR model. The analytical simulation and adaptive measurement are employed to investigate a seven-speed transmission. With both approaches, a detailed discussion about total transmission losses and individual loss mechanisms are performed under various operating conditions.