"You can't win," as a catchphrase, originated in the United States and was in use by 1950 (according to Eric Partridge, "A Dictionary of Catch Phrases American and British"). It expresses a sense of futility about hoping to succeed or, generally, to get something--anything--done. The elaboration "You can't win for losing," with its added play on logic, was around in the 1960s. It means that losing keeps you from winning; you can't win because things keep going wrong. People would say it when something unexpected or a bit of bad luck spoiled their plans.
(The word 'for' may be taken out of context here. It is not used as in "the flower was for her." For also means, because of or as a result of. i.e. "He could not think for jealousy." Which would translate "you cannot win as a result of losing.")