From the Super Mario Wiki
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If Team Mario passes the first Gate Space on any given board, they will be forced to battle a Whomp with six hit points by rolling Dice Blocks, similar to the Whomp battle in Perilous Palace Path in Mario Party: Island Tour. If a player fails to beat the Whomp, the Whomp is damaged and task is passed to the next player. If a player succeeds in beating the Whomp, each member of Team Mario receives two hearts before proceeding to the next segment of said board.
If Team Mario passes the second Gate Space on any given board, Bowser will hide the Star within three characters (including Bowser Jr.), and a player must guess who has the Star without any hints. If a player fails, the character with the Star knocks them back three spaces. If a player succeeds, Team Mario wins the game and Bowser loses.