{Image #411844} is first in order (circa 1939-40), followed by {Images #866287 & 866288} (c.1942) and {Image #411845} (c.1943-44). By definition, any copy with the "For perfect tone..." notice at left is a later pressing.
There is a slight difference even between the earlier Columbia labels that don't have the Columbia needles blurb. The licensing text on {Image #411844} reads "Licensed ... under U.S. Patents 1625705", whereas {Image #866287} and {Image #866288} read "Licensed ... under U.S. Patent No.s 1625705". I think the first one may be the earlier version, but would be glad if someone could provide exact dates for both versions.
Each side is from a different pressing, though both were from Bridgeport, CT:
- {Image #1844} was a 1940-41 pressing (the fine "Licensed by Mfr." print was original dating back to the red label's startup in September 1939, but the label artwork was reduced slightly and the fine print was brought closer to the "COLUMBIA")
- {Image #1845} was a circa 1943 pressing (the "Licensed by Mfr." variation was on 1942-45 pressings, and the "For perfect tone use Columbia Needles" blurb on the left was on pressings between early 1942 and early 1951)