I am no expert on Spanish Dependencies, but my Edifil catalogue shows an 1855 type l and a type ll overprint. The 1855 overprint has much narrower serifs on the "Y" and an angled serif rather than a horizontal serif on the "1". For the 1866 overprint the "66" is shown in the same place and typeface as yours, but the thin strokes of the numerals appear noticeably thicker. There are some experts on here that will be able to advise you on this in some detail.
I'd also like to find out exactly how to tell the genuine overprints from the plethora of fakes around. Those spaces remain empty in my album. I've seen several dealers who sell them as fakes, whether they are genuine or not.
I do have the Catalog pertaining to the Havana provisional Y1/4. These were only issued and used in Havana! It looks good but I'd need to compare with my book. I'm at work currently without it!
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