Dichloromethane (DCM) is extensively used around the globe in various applications, such as in closed industrial installations for food processing or pharmaceutical extractions (vitamins, antibiotics, etc.). In the coffee sector, it is used as an extraction agent for the decaffeination process of green coffee beans. Due to its low boiling point, ranging at approx. 40 °C, DCM can be easily removed subsequent to caffeine extraction by applying state-of-the-art solvent stripping processes. The intention of this study is to assess how much DCM, if any, is present in decaffeinated coffee packages as sold to the consumer, as well as how much of the extraction solvent residue is transferred into the finally prepared, consumable coffee beverage. This study sets out to highlight DCM contents of decaf coffees, directly taken from six EU countries’ supermarket shelves. In addition, DCM mass transfer rates from roasted coffee matrices into the corresponding, variously prepared beverages (drip percolated coffee, French press) are determined. All analyses were performed applying a Headspace-GC-MS technique. All presented data demonstrate that DCM residues in the 34 coffee samples analysed have contents well below the DCM maximum residue limits for roasted coffee both in the European Union (2 mg/kg) and the USA (10 mg/kg), with an average of 0.127 mg/kg, median value of 0.059 mg/kg and P95 of 0.444 mg/kg. Furthermore, this study shows that DCM mass transfer rates from the coffee matrices into the corresponding beverages have, for drip coffee, an average of 24.7% and median of 26.8%, and for French press, an average mass transfer of 41.9% and median of 43.1%.