Sadly, I do not have photos of most of my coins... and my memory isn't perfect either.
And while I don't think I actually have OCD, the question you asked made me really seriously consider just what
was my progress of oldest coins (particularly between 2008 and 2012; I'm fairly certain of 2002-07, mostly certain of 2013-15, and I'm not sure how much I can trust my memory for dates before 2002).
Now that the pre-2011 parts of my collection are not missing anymore (so far), perhaps at some point (hopefully soon) I might be able to assemble a reasonably full list (past 2002 anyway).
As a bit of a teaser, my last three (or perhaps four) oldest coins, which I do have photos of...

Coin #(x-2)
Ivan IV, post-reform wire denga, 1535-1547
This coin almost certainly held the position between mid-December 2012 and January 5, 2013 (circa 4:20 AM, forum time). Usurped it from a different, only slightly later, coin of Ivan IV that I sadly do not have photos of (which most likely held the top spot since 2010).
[EDIT: on further search, perhaps it didn't; I'm a bit unsure on dating a very late Tver pulo, which I apparently acquired a few weeks earlier, perhaps in October or November 2012.
No photos of that one forthcoming - I lost it sometime in late December '12 or early January '13, complete with the ziploc, and haven't found it again to this day. But there wasn't much to see on it anyway.]
[EDIT 2: apparently, modern research dates that type of Tver pulo to ca. 1545-1560. So while it might have been briefly my oldest coin after its purchase (likely around November 2012, as mentioned above) - I'll have to check the specific type of the 2010 purchase - it definitely stopped being the oldest after mid-December.]

Coin #(x-1)
Valens, Securitas (AE3?), 364-378 CE
Bought for Smackdown XXX. Held the position between ca. 4:20 AM January 5 and ca. 5:50 AM June 8, 2013 (both forum time).

Coin #x
Pantikapaion, tetrachalkon, ca. 210 BC
Sometimes I count it as my oldest, sometimes I don't (see below); definitely held that position between ca. 5:50 AM and ca. 6 AM June 8, 2013 (times approximate - I'm much more confident of the difference).

Coin #(x+1)
Olbia, dolphin, perhaps ca. 5th century BC
If this verdigris-addled piece of copper counts as a coin, it's my current oldest coin (since June 2013). I usually prefer the Pantikapaion coin above, which is at least pretty.