Upwelling leads to a sharp and strong decrease in water temperature in the coastal zone of the southeastern Baltic Sea. The quality of existing hydrodynamic models cannot fully meet the requirements of accurate upwelling forecasts. This study provides insight into the applicability of the simplified Ekman upwelling criterion method for the southeastern Baltic Sea. The upwelling criterion is the ratio of the vertical velocity and the duration of the upwelling wind to the mixed layer density. The vertical velocity was determined by the divergence of the integral Ekman transport in the transverse direction. Calculation of the criterion was based on wind data from NCEP/CFSR reanalysis. The upwelling criterion was compared with in situ temperatures from direct measurements near the D-6 oil platform taken in 2015–2017. Only 46% of calculated upwelling cases were confirmed by temperature decreases in the sub-surface. It was found that more than half of the cases of strong temperature decreases were caused by a northern wind (Ekman upwelling), when the criterion exceeded the threshold value. Comparison of the hydrodynamic model results and direct measurements shows that the model’s quality is far from perfect, and the simplified methods can be used as alternatives to models. Some recommendations were made for future upwelling research.