Both words in one sentence
- At least two skill checks in the Billy Vs SNAKEMAN storyline quests are not to succeed in what your character is attempting, but just to lose "in an awesome and non-fatal way".
Source: Heads I Win, Tails You Lose
- They succeed, but lose their most promising summoner and are buried under Masakado's body.
Source: Yank the Dog's Chain
- However, this is very risky, and if it doesn't succeed, then they immediately lose.
Source: Batman Gambit / Tabletop Games
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Google Ngram Viewer shows how "lose" and "succeed" have occurred on timeline