Do these 2 words mean the same?

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Does the phrase ‘A hiding to nothing’ have a similar meaning to “You don’t stand a chance?”

Never heard the expression "a hiding to nothing".

Maybe its some common Brit expression. But its not heard here in the US.

More or less, but I'd say hiding to nothing maybe implies more effort being put in or pain felt before the expected failure/loss.

I am on a ‘hiding to nothing’ trying to hook up with women in bars/nightclubs on the weekend

Examples with the lottery. Buying a one-off ticket you don't stand a chance of getting the big win. But if you keep throwing more and more money away that you could ill afford, buying more and more lottery tickets in the hope of the big win you'd be on a hiding to nothing.

What a weird and klutzy expression!

Its an ungrammatical sentence. If taken literally it means nothing at all.

Hiding....to....nothing.

The "nothing" part makes sense. Because that would be your payoff. Nothing.

But 'hiding'? What does THAT have to do with it?

Hiding, concealment, being secretive... none of those things are involved (if you two are using the expression right).

you're not 'hiding' anything. you're making a 'bad investment' in effort, or money, or whatever the case.

^ I guess it means hiding as in beating. In other words you are subjugating yourself to harm but will likely get nothing in return for your sacrifice.

Never heard that expression here, either. Very strange expression.

I am on a ‘hiding to nothing’ trying to hook up with women in bars/nightclubs on the weekend

I've never heard of the first phrase. But then again people from different countries use expressions that I've never heard of and get confused by all the time. For example, not long ago someone used the phrase "threw a wobbly", and at first I had this mental image of someone throwing a Weeble or some other toy that wobbles but doesn't fall down.
Then I realized it must mean the same as to "throw a fit", as in losing one's temper.