Hey there, I felt like i'm obliged to answer your question and really because this thing happened to me too and it's really annoying since:
1. i can't come up with the right keywords to google the symptoms of this event and it took me hours to find your thread after putting "gmail chronological sync problems".
2. so far only you share the same problem
Regardless the fact that I use iPad and iPhone and the event happened to both of my devices (regardless of the mail app i used),
I reckon the solutions should be similar to an extent.
In fact, i can't even consider this a real solution. So here's what i did:
SOLUTION:
instead of fetching 50 most recent emails, i changed the setting to fetch 200 most recent emails.
Suppose that previously, my gmails sync all emails properly only from period of today until last month before it actually made the "jump" to last year
(skipping a lot of important emails between those periods).
what the solution does is tricking the gmail to sync at least to a longer period (say, from today until last 2-3 months) before it made the "jump" to last year (still skips some emails)
Thus, i mentioned this is not really a solution
I'm not sure whether this is server problem, or just my firmware or setting problem. but my desktop mail client is doing fine; synchronizing all the way from the most recent to the oldest emails.
I do realize the problem turns up after i switched from thunderbird to outlook 2013 as default mail client. not sure whether this didn't happen before or this had happened and i only just realized
pls help find real solution