Charles,

Fair Play is a village in west Polk County. COL Thomas Roe Freeman's command was mostly recruited from south-central MO from Rolla in Phelps County (near Freeman's home)south into Arkansas. COL Freeman's command was part of MG Sterling Price's great MO raid, and before Price took his battered command back south to Arkansas in early November 1864 bits and pieces of his army were already straggling back south from all over Missouri. It seems to me that your ancestor and perhaps comrades were trying to make their way back to Arkansas before pursuing Union forces gobbled them up and ran into grief at Fair Play. At that time there were skirmishes all over southwest MO involving those straggling pieces of Price's army running into Union patrols. Freeman had only 250 of his men left at the end of the raid.