Can't Win For Losing Edit Meaning

1.

A phrase meaning that things would be going great for you if they weren't going so badly.

"Well, my girlfriend dumped me, my dog died, I got fired from my job, I went to grab some fast food to make myself feel better and on the drive back I got a flat tire, and when I finally get home I realize they screwed up my order."

"Damn, you can't win for losing."

See shitty, wretched, unlucky, bad juju