On one side of the water: Big Mom's Grand fleet as seen during the latest chapters' sea battle. IE: Hundreds of Tart Ships, hundreds of gingerbread paddle-boats, several different unique ships of the individual Big Mom Pirate children, the Queen Mama Chanter and the Candy Sea-Slug Homie. In addition to all that; Bege's Notra Castello, the floating kingdom of Germa 66 and the Sun-Pirate Allies including Wadasumi allowed as support from the water. Vs The legendary ship, the OroJackson. All of the ships are fully supplied and all in pristine condition. All of the Big Mom fleet is outfitted with Candy-jacketed ammunition. The starting distance is 1 km away. Fight takes place off the shores of Cacao Island. Round 1: Each side has suitable numbers of each group's generic fodder for piloting said ships. No named or otherwise special characters in this battle. Truly just ship vs ships. Round 2: The present day remains of Roger Pirates (sans Shanks) are on the Orojackson. The Big Mom Fleet includes their full roster minus Big Mom herself, which includes the full Germa, the Firetank Pirates, and the Sun Pirates. Round 3: The present day remains of Roger Pirates (including Shanks) are on the Orojackson. The Big Mom fleet still includes everybody as well as Big Mom herself this time. Round 4: Gol D Roger is alone on his ship. The Big Mom fleet still includes everybody they had from Round 3. Round 5: The olden days Roger Pirates, as we see in chapter 0 against Shiki, vs The Big Mom fleet from Round 3, with the addition of the Giant Warrior Pirates including Dorry, Broggy and Harujin, their crews and several of their longboats assisting the Big Mom Fleet. Victory is by destroying all of the opponent's ships to the irreparable state that so much as bringing it a kilometer back to Cacao Island would be impossible. No "claiming" your opponent's ships. I think that The Big Mom Pirates take Round 1 easily, Round 2 without notable difficulty, that Round 3 is the toughest for them yet, but still with them as the clear winners, Round 4 as an easy win for the Big Mom Pirates due to how difficult it would be to maneuver a ship by yourself, and Round 5 becomes a utter miss, but ultimately has the Roger Pirates losing high diff in the face of absurd firepower.