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Itadaki Street Special is the fifth title in the long-running Itadaki Street series. While earlier titles had references to the Dragon Quest series, this one prominently features dozens of characters and boards from both Dragon Quest and its once-rival Final Fantasy, not to mention copious other fan service such as arranged music.

The same basic gameplay of the previous titles is retained -- players move around the board purchasing properties and investing in districts to earn money -- but this is the first title in the series to make any significant changes to the game's structure with the introduction of the level-up system. Rather than simply counting laps around the board, players earn EXP from various actions such as collecting suits or reaching the bank, and leveling up will increase the money they earn when reaching the bank. The game has also been rebalanced to be more forgiving to novice players, along with a wide range of other minor changes.

The main new mode in this entry is the "Sphere Battle" mode, which replaces the chance card board with so called Sphere Dice, resembling the Sphere Grid from Final Fantasy X, and which causes various random effects to occur when it is rolled.