Potential answers for "Win some, lose some"

⭐⭐⭐⭐ COMPROMISE
⭐⭐ DARNEDIFIDO
⭐⭐ CANTWIN
⭐⭐ YOYODIETING
⭐⭐ IDIOM
⭐ SNAP
⭐ SEMIFINALIST
⭐ SHED
⭐ GOROUNDTHEB
⭐ RIPEN

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Had charge of   '20s or '30s   Organized excursions