I love the character of these old labels. This design seems to date from about 19oo. Hand-lettering -- note the variation in letters such as C -- but some features are familiar. The "Detroit" angled serifs are used in fonts like Brothers http://www.myfonts.com/fonts/emigre/brothers-ot/ but here the letter-forms are rounded instead of angled.
Don

MANUFACTURED ONLY BY THE PRAIRIE CITY OIL CO.: I guess you could easily combine Billhead 1890 /C and 1900 style.
WINNIPEG LIMITED: some kind of hand-drawn Gotham, Garner or Egyptian may do the job.
UFFALO: concur with Don on 'Detroit serif' style; Fairplex might work as well;
OIL: same 'Detroit serif' style but /O reminds me of something... Should check the rest of Letterhead Fonts...

Yeah, I was going to say, Fairplex is the Emigre "Detroit serif" font, Brothers is more of a Latin-meets-Grecian. Easily confused though, Emigre fonts with similar expressions and evocations. :)

MANUFACTURED ONLY BY THE PRAIRIE CITY OIL CO: I agree with Ryuk that Billhead 1900 is a good starting point for duplicating most of the letters, modified by adapting the top half of Billhead 1890 for the _C_. You have to do a fair amount of clipping of some but not all mini-serifs, flatten the dished ends of the strokes, and do various adjustments to get it right. I would use the lowercase version of the letters:

Great finds. Billhead looks like a great starting point. I thought about recreating the letters myself in Illustrator but was having trouble seeing the detailing on the serif style in my sample. Does anyone have access to some early 1900 type specimens? Any online resources.