The 16-0 season on Community Clown College, shame it didn't work out in playoffs but everyone on that team was awesome and I still love those guys.
Playing a 2 1/2 hour match on cp_ashville aka cp_auschwitz (and winning, thank god).
This game with Pwr Rangers: http://play.esea.net/index.php?s=stats&d=match&id=3198119
Not only was it a true testament to how hard our team had worked that season, going from a low IM shitter team to a contender, but it was the last game I played on esea.
More recently, winning the TF.TV HIGHLANDER INVITATIONAL was pretty awesome, just one magical day where everything seemed to go incredibly right. I know everyone on our team had a great time that day too.
Finally, this one particular scrim is stuck in my brain: http://sizzlingstats.com/stats/64614
It was the last time I made a serious effort to succeed in 6v6, and the game went well and confirmed that, if I really tried, I could build a strong team for main or invite.
...And then everyone decided not to join that little project right afterwards RIP.