Put it immediately after the bump or spin-out, just before the close-up reaction, so it marks the turning point in the clip. Follow it with Roblox Oof for a second hit, or with No God Please No when the fail gets even worse.
About this sound
This is Luigi's long, wobbly hurt yelp from Mario Kart 64, a stretched 'ow-wowowowowowow' lasting under two seconds. It sounds bright and cartoony, turning a crash into something playful rather than harsh, and it gives a quick burst of comic frustration. The voice comes from the Nintendo 64 racing game released in 1996, where short character reactions played constantly during races.