This plugin allows your players to gamble with tokens (from TokenEnchant plugin) or money (through Vault plugin).  You simply create a coin flip session by selecting your colour and amount you wish to bet.  Once your session is created, any players can accept the bet and possibly double your token/$.

Creating "coin flip session"
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Accepting "coin flip session"
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/cf help : displays the help menu
/cf reload : reloads the config.yml
/cf debug <true|false> : turn on/off debug mode
/cf <amount>[token|$] : start creating a coin flip session.  If the currency type ['token' or '$'] is not specified the default currency specified in config.yml will be used (default : 'token')

Simply drop CoinFli-x.x.x.jar file into plugins folder and restart your server.