Milkability is defined as the ability of an animal to give a regular, complete, and rapid milk secretion by the mammary gland in response to a proper milking technique. Indicators of milk production and milkability of ewes were determined in 359–370 ewes of 9 genotypes. For each ewe, the milk flow was recorded during the individual control measurements. The amount of milked milk was measured in individual time intervals after the attachment of milking cups to teats on udder of the ewe (10 indicators). We processed the obtained data using the REML methodology, with the MIXED procedure of the SAS statistical package. All indicators characterizing milk production and milkability of ewes were statistically significantly influenced by the genotype and the control year factors (p < 0.001). The order and stage of lactation were also significant factors in some cases. The machine milk yield of the monitored population of ewes was 318.26 mL on average. The total milk yield was 436.58 mL and the machine stripping ratio was 27.73% on average, ranging from 0 to 95%. The highest machine stripping ratio was determined in the Lacaune breed (37.69%), which had the highest total milk yield (524.69 mL) and one of the highest machine milk yield (332.70 mL). Compared with purebred Tsigai ewes and ewes of the Improved Valachian breed, crossbreeds with specialized dairy breeds (Lacaune and East Friesian) had better milk production and, in some indicators, also better milkability.