Alneyan vs Joachim: Year 2403.5 or so.
It hurts. Joachim managed to repel my attempts to invade his systems while retaliating and disabling my excuse for a fleet. (Seeker ship vs seeker ship, heads or tails?) Of course, lagging behind in research and not having mines does hurt. A lot.
However, while my Empire was on its knees and very near surrender, Joachim didn't deal the coup-de-grāce. How merciful he is.

Happiness was decreasing everywhere, and my radioactives storages were a mere two digits. Winning a few other battles would have probably spelled massive riots, and as such, destruction of the Arcadia League. Still, my Empire is in a very poor shape, with slightly more than half the galaxy under its greedy hands. (But the worst half as far as I know) But as long as there is hope, we shall not surrender and we will stand to the mighty frigates of our oppressor in our finest hour and... I digress.
Joachim played well, unlike me as I am playing one of my worst games, on par with my slaughter against Geoschmo. (As know as, why putting ECM, Combat Sensors and training the ships isn't optional, unless winning is also optional for you) Researching Destroyer rather than Mines being quite a big mistake, as these little shiny devices would have been able to keep Joachim at bay so much more efficiently than these so unreliable missile ships. (Is a missile ship ever working properly when in the hands of the non-entity known as an AI? Nodachi had problems with these as well in our game.)