American Express used two main styles of printed cancel, one with serif lettering and one without. They also used a partial type of year dating for printed cancels during the last two years of the 19th century by leaving the last digit of the year incomplete. Thus 189x would be completed with an 8 or a 9 by hand. Or at least it was supposed to be. Often the 189x would be left that way.
Serif lettered printed cancel for 189x. Rouletted stamp likely used during 1898.
Rouletted sans serif 189x.
Hyphen hole 189x sans serif with 1900 manuscript cancel. The use of hyphen perforations began sometime in December 1899. My collection has no hyphen hole stamps cancelled in November 1899, though there are several canceled in December. The stamp above was probably cancelled with a printed cancel in 1899. An Amex office was using up this old supply when they used a manuscript cancel on January 12, 1900.