I know it's a sporting reference but not sure which sport. It means someone's had five goes at something but has so far scored zero.
Doesn't have to be 5.
If I've had 3 attempts at making a decent risotto (for example) but so far they've all been disastrous, I'd say I was O for 3.
So he's taken part in 5 staredowns and won none of them.
Retired English Teacher