My most memorable and proudest moment was where I kicked my friends ass in Rome: Total war. I was playing the Greek Cities faction and he was playing the Carthage faction and we were having a seige match (with me being beseiged). I made a few retarded moves and didn't notice the ladders he sneaked in, and next thing I knew my ranged units were getting raped and alot of my hoplites destroyed. But when he entered those streets to face of my Spartan Phalanxs, he was a goner.
My most shameful gaming moment was also in the same match, where in my overconfidence, I charged a retreating unit with my spartans only to get charged down by Elephants when they entered a square. Boy, did I feel stupid.
Despite my heavy losses, I still won thanks to my awesome general unit, which I also chose to be Spartans