I played with Ymir when he used to work for GoA (so he wasn't red at the time) (goa were in charge of LoL in europe at a time, incredibly bad times)

If I remember correctly, we won.

I've been against Loote and another red (I can't remember who it was) in solo queue before.

Morello and Kismet

went solo mid(kennen) against pendragon(vladimir)

I played with Udyr once through a premade deal, and we randomed against Pendragon on the other team.

played against Riot Guinsoo, not sure if he lagged out or rage quit, but he left the game..

A few times. First was with Guinsoo, then Serif, and then Tobster (I know I spelled his name wrong). Amusingly enough they've always been on my team.

riot tobi.... his ww ... lol

I played a game with phreak once, he was Ashe and I was Zilean. He did a good job directing the team, and we won.

I also played 3 games in a row once vs pre-arranged rioters(5 v 5). Me and some friends, never done ranked arranged teams before, queued up one night. I guess we were the only 2 teams queuing up. We won the first one, and lost the last 2. Pendragon plays a pretty mean Yi.