Eary Dated
Here is some more information. Alfonso VIII (1158-1214) issued many types of billon dineros and obolos, including the one type dated ERA MCCIIII . These rare billon coins dated 1204 in the Era of Safar, commemorate the restoration of Alfonso VIII to the throne of Castile, and mark the end of the regency of his uncle Fernando II of Leon” (my translation). These are rare and unpriced. I think a few have been sold recently. To quote Sean Breazeal from his forum: http://www.medievalcoinage.com/index.htm
Probably the earliest European dated coins of all are Spanish coins minted by Alfonso VIII in imitation of the Moorish coins whose issuers were slowly being driven out of the Iberian peninsula. They are dated using the contemporary Spanish or Caesar Era, sometimes referenced as the Es-Safar, calendar system used in Spain at the time which dates 38 BC as its year 1. A few types are known. One is a series of gold dinars dated from 1223 through 1255 SE (1183-1217 AD), two others are an obol and a denier of 1204 SE (1166 AD). In January 2007 CNG sold the first confirmed 1204 Spanish Era dated denier, all previous dated examples being oboles. These latter two coins are probably the first coins on the European continent to have ANY date written with Roman numerals MCCIIII, the dinars have the date written out as Arabic words rather than numerals (such as writing "Two Thousand Seven" on a modern coin instead of 2007). Here are two from my collection.
The date is on the left image: ERA M C C I I I I . Less than 10 known, 5 in museums and 5 for collectors to fight over.
Once again the date is on the left, starting at 8 o'clock. ERA MCCIIII. Less than 8 known, 4 in museums, 4 for collectors.
I hope this helps. I'm very fortunate to own the 2 that i do. Two of the trophies of my collection.