Potential answers for "Challenging bet"

⭐⭐⭐⭐ EXACTA
⭐ IOU
⭐ REWAGER
⭐ SEE
⭐ BIPPY
⭐ ATSTAKE
⭐ RAISE
⭐ OPEN
⭐ GONER

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Frequent co-signatory   Southernmost major U.S. city   Edward VII, familiarly