Hi, The glasses are almost certainly cocktail glasses from the inter-war years (most likely early 1920s to 1939). Cockerels in various forms were a very common motif on cocktail glasses, I have approaching 1,000 and have not seen these particular glasses before. I have one set with engraved cockerels on a similar glass blank, all clear glass, but with a slightly different stem arrangement. I have no idea where, far less who made them. A set of 6 glasses commonly had 3 or 6 different views of the cock fight starting with "set to" and ending with "the death" where the winning cockerel stands proud over his dead opponent.
Hand enamelled glassware was most commonly produced in Czechoslovakia, before 1918 part of Bohemia. Other countries also produced hand enamelled glasses but the largest producers after Czeckoslovakia were UK and USA. In my experience the best quality cocktail glasses decorated with cockerels are from USA. For obvious reasons, production stopped around 1939 in Czechoslovakia and UK. If they are US they could be slightly later.
Most hand enamelled cocktail glasses had a transfer printed outline applied to the glass for use as a template for the decorator. You may be able to see black outlines on the cockerel. The ground/grass/background is more usually left to the individual decorator's discretion so is less likely to have evidence of a transfer print. The glasses look to be good quality with a coloured bowl and clear stem.
Sorry I cannot offer any more information on maker or country of origin.