My entire youth sports (below high school) was a long running embarrassment yet with nothing remarkable. My fat ugly nipples in middle school track tank tops might have been one of the worst. Wrestling in 2nd & 3rd grade was moving from one mat of degradation to another.
Senior year of football in a first round playoff game, against another small town school that took football very seriously and traveled well. I wore old school knee braces that had these hanger straps that ran up the inside of the pants and hooked on the belt. Damn things were constantly coming undone. In this case, the braces became terribly tangled up and I could barely move because they slid down so far. I came off field following an offensive series, went to far side of bench, and without thinking much dropped trow to fix the situation as quick as I could. I gradually become aware of a commotion behind me, and turn around to see that I'm directly in front of the visitors section and am being heckled by the cheerleaders, students, and parents. Good tims.