Where did the expression, "I can't win for losing" come from and what does it mean

This is a fairly old expression, I heard my Dad say it in circa 1950.

I googled a few explanations from searched phrase, and I didn't encounter one that really catches the spirit. Sure, it basically means, "I'm a loser" but it is said with a touch of humor - something along the thought process of 'I never win. Maybe I could win for never having won. No... I can't even do that.'

Similar in spirit to the words of the blues song 'Born under a bad Sign' - "If it wasn't for bad luck - I wouldn't have no luck at all..."

As a teenager in the 60s I was a training jockey on the horse racing circuit and that's where I learned this phrase. I believe it originated from horse racing because at that time at the lower level horse races you only got paid if you won the race came in first. The second and third or fourth place didn't get paid anything we're at the big stakes races like the Kentucky Derby or the Belmont first second and third all got paid. So at the higher level races you could win money even though you lost and you could also get into bigger races because you placed which means you came in either first second or third. So if you were in one of these lower-level races you couldn't win for losing you had to win the race in order to win. So more or less in those lower-level races you could not win if you lost the race but in the higher stakes races you could win even if you lost. So people on the racing circuit or jockeys or owners would only need to say I can't win for losing and that would describe the type of race you were in and what at what level you were racing. Hope that helps it's kind of convoluted I don't know how to explain it well LOL

Elephind and Google Books searches dig up examples of the expression going back to the 1920s. The oldest match is from Johnny Dope, "Squints at Sports," in the [Urbana, Illinois] Daily Illini (May 13, 1920):

Out of 21 starts the Detroit Tigers won six games. They can't win for losing.

From Making Paper, volume 9 (1926) [snippet view], which has the expression on page 180:

We have a little lady in our office who just couldn't win for losing. She didn't have to holler "come you 'leven." She always drew it.

and again on page 215:

Somehow Mr. Hanny couldn't win for losing.

Also, from "Canyon Splits With Warriors at Local Field," in the [Abilene, Texas] McMurry War Whoop (May 5, 1928):

"Can't win for losing." That seems to express the results the Warrior ball players have been meeting in their recent skirmishes on the [baseball] diamond. Canyon was successful in taking the first of a two game series here last week, although the tribe came back to win the second. Up at Tech this week, the tie was played off and the Torreadors proved the better. That 25-20 game, with the Indians on the heavy end, was a feature of the trip.

And finally, from "Temple Hard Luck School," in the Breckenridge [Texas] American (December 7, 1928):

TEMPLE [TEXAS], Dec. 7. (AP)—Temple is extolling a high school football team that "couldn't win for losing," which lost most of its important games, but which always gave the home town rooters a tremendous thrill.

In the eleven games which Temple played the Temple captain tried to call the toss of the coin every time—and failed eleven times. In every game that the team lost it gained more yards than its opponents. It won the only game in which it was clearly outplayed, on the basis of yards gained.

In its final game, the game which it most wanted to win, it outgained Waco in almost every department except scoring. For a few seconds the Temple defense wavered and Waco won, in spite of the fact that Temple had thrown the Waco team for almost as many yards loss as gain. The yards that Waco did gain were the ones right next to Temple's goal posts. Temple rooters are in favor of repealing the law of averages.

This last account suggests that an early sense of the expression was that the person or team that "couldn't win for losing" performed well in every facet of the task except succeeding in it. However, it may be that other early users of the term used it merely to mean that the person or team couldn't get out of its own way and was destined to lose because it simply didn't know how to win.

As other answerers and commenters have noted, "can't win for losing" has lots of companions in phrases that seem to express kindred sentiment—including the one featured in 1967 Sam and Dave song "I Can't Stand Up for Falling Down", memorably covered in 1980 by Elvis Costello.

It is an expression of the unfairness of the universe that the speaker is experiencing. He is saying that in a fair universe, you allow for losses, and you expect to be rewarded by gains, they tend to balance. But in this unfair universe, the speaker has given many losses but has not received one win.

Sven's answer was informative. My late dad used the phrase multiple times when we were in Texas in 70's and 80's. He used it in the sense that no matter how hard he tried he couldn't win.

The meaning is clear to me linguistically. You can win for ... What are the common answers? Getting first place, getting highest score, etc. If your luck is so bad, then even if a condition of winning were to lose, you still wouldn't win. It's hyperbole.

My mother used this expression, and, yes, I think it was in the sixties. It meant just that the person was a sad sack, but I always understood it literally to mean that the guy is such a loser that if there were a prize for losing, he wouldn't even win that.