Potential answers for "Play for higher stakes"

⭐⭐⭐⭐ UPTHEANTE
⭐⭐ DRIVEUPTHEPRICE
⭐⭐ SOARED
⭐⭐ RITA
⭐⭐ TRIFECTA
⭐ ESPN
⭐ ARCADE
⭐ LATOSCA
⭐ SCRUM
⭐ SIMPLE

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Troubled greatly   Calendar rows: abbr.   Flat rate?