winning toss

[georgemartin22]

What does the "winning toss" mean in the following sentence?:
I haven't had a "winning toss" for a while.
Does it mean he/she has been going through a difficult period?

Is it an idiom or a Metaphor or simply the act of tossing?

 

[digitS']

Although I know little about gambling, I believe the first throw of the dice, if it comes up 7 or 11, is a "winning toss."

If the dice do not add up to 7 or 11, subsequent throws must be made to win. The risk of loss increases/winning becomes more difficult.

It would be lucky to have a "winning toss" on your first and every turn. So, Gillnetter's explanation would also be correct.

Steve