I'm assuming you did not intend to count metal detecting find as "circulation"? For many members here, these would be the oldest otherwise. Doesn't really matter in my case though (as I've never tried metal detecting).
Oldest overall: 1935? Soviet 1 kopek
A ground find from around 2004. I wasn't really collecting back then, so I almost immediately gave it to a classmate, never seen it since. Don't even remember if it was 1935 or 1936, actually.
Oldest non-ground find that was likely from circulation: 1955-S
Wheat centBack in 2012, several non-collecting relatives got me a bag full of coins for what was probably supposed to be my 20th birthday. I have no idea where they got them, and the bag had some obsolete Israeli coins so not all of them were from circulation, but the 1955-S cent very possibly was; I definitely hadn't heard anything to the contrary. (The bag had a few other American coins, but they were all much more recent.)
Oldest cash register find: 1961 Soviet 20 kopek
I think I need to clarify - this category is coins that were saved for me by friendly cashiers at places where I'm a regular customers. I often see assorted coins from the 1990s there, a few from the 1980s, some from the 1970s; the only 1960s coin was this 20 kopek. (Not really unusual otherwise, there were a lot of them made, and they circulated up until 1991.)
I almost got an 1800s (as in the decade 1800s, i.e. over 200 years old) coin in this category; there was a bit of miscommunication with the cashier, and the coin was given to another guy. I have no idea what it was doing there in the first place; I still don't have that type either.
Oldest I know was from recent circulation: 1965
Washington quarterFrom my uncle's wallet in December 2009. He knew I collected coins, but wasn't interested in them at all, so he knew his wallet was just regular
US coins - but had no problem with me getting a few anyway. I picked out the 1965 quarter, some
State Quarters, and a Lincoln Presidency cent (that just went into circulation that November).
Close second, and technically beating it by time in circulation, is an 1969
Memorial cent I got from a US tourist I did an impromptu tour for in 2014.
Oldest I got in change myself: 1985 Israeli 1 sheqel
I hadn't been to many countries - after the age of two, at least - that
didn't change their currency in the 1990s or later. In fact, ignoring whatever was going on with mid-1990s Russia (where the pre-1990 coins - all the way back to 1926 - were technically still legal tender but had such tiny face values they never circulated in practice), Israel seems to be the only exception.
I've been there a lot of times, including a few before the age of six, but I can definitely say 1985 was the earliest coin, because I know I did get an 1985 sheqel, and I know that was when they changed the currency.