I am having the same issue. I use Pocketmoney on Mac OS X. On the iPhone everything looks fine, when sorting by date.
Here a sample-sorting (should be ascending from top to bottom):
In this example, bookings from June are inbetween bookings of May.
Pocketmoney 2.0.3 (215)
Mac OS X 10.7.4
Regional Setting: German / Austria
Date Setting: Gregorian