I’ve heard it with and without the “and.” Supposedly using the “and” is British practice, but my very American seventh-grade math teacher in West Texas insisted we all use the “and” when reeling off numbers like that. (There have been whole threads on this.)
I have heard all of the following to describe 2014:
twenty fourteen
two thousand fourteen
two oh fourteen
oh fourteen
twenty oh fourteen
I know the last one doesn’t make sense. Nonetheless, I have heard it.
To answer the OP, I would say our ancestors back in the early 1900s said either “aught” or “naught” but they might have said “oh” as well.
As for the second question, there are many situations where we say “oh” and we mean zero. Telephone numbers, for example. In the song “Pennsylvania 6-5000”, the chorus says “Pennsylvania six five thousand” several times, and then once it says “Pennsylvania six five oh oh oh”. That’s from the year 1940. Another example is model train gauges, which include H2, H1, and H0, read out loud as “aiche two”, “aiche one” and “aiche oh”, respectively. And there’s street addresses, two. I used to live at 309 Bowden drive and we pronounced it “three oh nine”. That was in the 1970s. All these examples are BEFORE it became common for everyone to have a keyboard attached to their computer. Back in 1980, most people didn’t know how to type unless they planned to have a career working as a clerk or a secretary.
Nitpick: it would be more accurate to say tic-tac-toe is an Americanism for noughts and crosses, since the latter predates the former (though the name tic- or tit-tat-toe was in use at around the same time to refer to some other game.)
Or possibly turn of the millennium to fully distinguish it from 1900.
I’m puzzled.
Did you used to say “One thousand, nine hundred and ninety-five?” Or, “nineteen-ninety-five”? Why does “two thousand fourteen” seem more proper to you?
For one, because I didn’t say “twenty-oh-one.” Saying “twenty-fourteen” just feels crass. (I also say “one thousand” for the century that was 1000 years ago.)
Battle of Clontarf, 1014. Universally pronounced “ten fourteen”.
Battle of Hastings, 1066 - “ten sixty-six”.
Well, if you’re talking about using I for one on a typewriter I think Cecil wrote a column about that (typewriters didn’t have a key for the number one), but I can’t seem to find it.
As for the letter O and the number zero I’d say it’s a combination of them being essentially identical when written, and the fact that the last syllable in zero is “oh”. They probably don’t do it in the UK because they don’t call it zero, they call it naught.
Not when I say them. Therefore, not universally.
You are alone. I have never, ever heard these dates called anything else.
I will bet you 100 baht I am not alone.
I believe you. Where did you grow up, may I ask? I grew up near New York City.
I grew up in West Texas, but I doubt any of the rednecks I grew up among even thought about the 11th century much if at all. And that was quite a ways before the 21st century.
Or, more recently, 867-5309.
Don’t take this this wrong way…but that might explain it. Many folks first hear “ten sixty-six” from their junior high or high school history teachers, but maybe it didn’t make the cut where you were.
What gets me is before the year 2000, two -oh-oh-oh I guess, years were always 2 digits, 1997 was pronounced ‘ninety seven’, they we went to this 4 digit system. Why 
Was it we were all so frightened by the y2k bug that we somehow vowed to always use all the digits from this point forward? Can we get back to the shorthand of just the 2 digit year?
They should be sleeping then anyway 
I hear it all the time, especially in reference to the “oh” years. Like, for example, “I returned to the US in November of oh-three.” Thinking about it, I don’t seem to hear it as much for 10/11/12/etc.