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Unlock Legends Mode
In the Challenge mode, you must unlock Challenge #62~#66. Completing these Challenges will unlock Challenge #67, the Legends mode.
#62~#66 consists of finishing Arcade races in Normal or Hard mode. The description of the criteria in the Challenge screen says 2+ Laps so a win in Easy mode will not unlock the Challenge.
The Legends mode is exactly like the Arcade mode but you only race against the 5 'Legends'. All 5 of them are good riders and they almost always ride as a pack. They are tough but certainly not impossible to beat. Challenges #68~#71, which have no winning criteria shown until #67 is unlocked, are beating the legends in the Legends mode. Good luck!