After analyzing it again there is most likely an error message logged by
Diodon when starting up when this error appears. As I am not able to
reproduce the bug do I really need a log file to see what exact error is
thrown.

I have done some testing and it is actually possible to change Diodon command 
in the Startup Applications Preferences to the following:
bash -c "G_MESSAGES_DEBUG=all setsid /usr/local/bin/diodon 
&>/home/user/diodon_debug.log"

replace user with your username. Whenever Diodon is now started it will
log into diodon_debug.log. When the error occurs simply attach that log
file to this bug (log file is overwritten each time you startup your
machine again, so it won't grow to an infinite size...)

Thanks for your help.

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https://bugs.launchpad.net/bugs/1383013

Title:
  Diodon on 14.10 does not clear history consistently

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