Both words in one sentence
- No-Gear Level: You lose all your gear when you're made a slave by Kreo and taken in a keep east of his town; you must resupply you with armours/weapons looted of dead enemies or stored in the keep.
Source: Video Game / Nehrim
- While Popeye tries to help her lose weight, Brutus tries to get her to keep it on.
Source: Chubby Chaser
- Contrast Continuing Is Painful, where you lose a lot more than expected should you decide to keep going after you lose.
Source: Death Is a Slap on the Wrist
Google Ngram Viewer shows how "keep" and "lose" have occurred on timeline