It's definitely possible if you're jumping big waves and are landing sideways. If you're landing sideways at the bottom of a large wave and it caught your boat at a sharp angle (something close to 90 degrees), the momentum could flip you over. But these would have to be pretty good size waves. I doubt any waves generate by wakeboard/ski boats would be big enough for that. If you're out in the ocean, I would be worry about jumping and landing sideways.