But...Dash mentions carrying the flag when she was a filly, but as we saw, Cloudsdale didn't get the Games. Unless Cloudsdale Elementary students were part of the this scheme too in the day and she carried it for another nation.
Cloudsdale would have competed. The CMCs are carrying Ponyville's flag at the Crystal Empire, after all.
That was a great episode. Loved the song, and the animation that went with it (especially the gag at the end). Would have liked a bit of Mane 6, but I guess that would have taken time away from a good storyline.