Pip's Magic Pirate Flag first appeared in the episode "Pirate Genie-in-a-Bottle!" Jake and his crew discover Pip's ship-in-a-bottle and couldn't wait to make wishes of their own. But as Pip attempt to make their wishes come true, he would accidentally conger up frogs as his magical powers are running out. He knows of a location in Never Land called the Treasure-Wishing Well in order to restore his powers. While on the hunt for the well, Pip is asked by the young pirates what he would wish for. Pip admits he would wish for a ship of his very own so he'd sail the Never Sea, however pirate genies aren't allow to grant their own wishes. During their travel to the Treasure Wishing Well they come across a large windy canyon that proved to strong for Pixie Dust to be of any help,However Pip knew of abetter means to cross as summons his Magic Pirate Flag from his ship-in-a-bottle.As Pip and Jake's crew took off through the sky Captain Hook jumps and hooks onto Pip's flag as it takes off; Hook's crew one by one jumps and grabs one another, dangling from the flag.However Hook's hook rips into the flag causing it to unraveling causing Hook and his crew to panic as the flag's thread becomes longer.Jake grabs the thread as Pip lands the flag on the other side of the canyon. As everyone disembarks, Jake ties the unraveled flag around a rock to anchor Hook and his crew to the ledge.
The design of the Magic Pirate Flag is loosely based on the Magic Carpet from the film, Aladdin, such as having tassels for hands and feet.