The Heavenly Demon, ruler of the underworld, Donquixote Doflamingo
Vs
The natural-born monster and one of the 4 Yonko, Charlotte Linlin, aka Big Mom
Scenario 1:
Location: The Seducing Woods
No interference, no extra intel, both have intent to kill
Scenario 2:
Location: Going Merry in the middle of the sea on a cloudy day
Big Mom is starting to get hungry. Doflamingo has full knowledge of Big Mom’s past. He is carrying a picture of Mother Caramel, and knows the entire story and the effect the picture has.
My thoughts:
For scenario 1, Doffy loses but still manages to push her to high diff. He has a huge speed advantage, and can use awakening to distract her and even manipulate her. I’m assuming that parasite is useless against her. He can tank G4 head on even after being nerfed with Gamma Knife. Jinbe can block Napoleon with his bare hands, so it’s safe to say that Doffy can do so easily when using strings. With his endurance and speed, BM will have a hard time finishing him off. On the flip side, Doffy will have a very tough time inflicting any damage on her.
For scenario 2, Doffy wins high diff. Using his intel, he can shut down BM’s iron skin at will by tearing up the picture of Caramel, and can be prepared for her shrieking. This can allow him to at least injure her. An injured, angry, hungry BM turns into a weakened, starving BM in a matter of hours. Doffy can take to the skies and keep her busy. Once she’s starved enough, he can push her into the water and finish her off. No one to rescue her in this scenario. If Jinbe were able to do so, this won’t be a problem for Doffy who is his superior in every way.
Vs
The natural-born monster and one of the 4 Yonko, Charlotte Linlin, aka Big Mom
Scenario 1:
Location: The Seducing Woods
No interference, no extra intel, both have intent to kill
Scenario 2:
Location: Going Merry in the middle of the sea on a cloudy day
Big Mom is starting to get hungry. Doflamingo has full knowledge of Big Mom’s past. He is carrying a picture of Mother Caramel, and knows the entire story and the effect the picture has.
My thoughts:
For scenario 1, Doffy loses but still manages to push her to high diff. He has a huge speed advantage, and can use awakening to distract her and even manipulate her. I’m assuming that parasite is useless against her. He can tank G4 head on even after being nerfed with Gamma Knife. Jinbe can block Napoleon with his bare hands, so it’s safe to say that Doffy can do so easily when using strings. With his endurance and speed, BM will have a hard time finishing him off. On the flip side, Doffy will have a very tough time inflicting any damage on her.
For scenario 2, Doffy wins high diff. Using his intel, he can shut down BM’s iron skin at will by tearing up the picture of Caramel, and can be prepared for her shrieking. This can allow him to at least injure her. An injured, angry, hungry BM turns into a weakened, starving BM in a matter of hours. Doffy can take to the skies and keep her busy. Once she’s starved enough, he can push her into the water and finish her off. No one to rescue her in this scenario. If Jinbe were able to do so, this won’t be a problem for Doffy who is his superior in every way.
Big Mom would take Doffy's soul, just like that. He would shit himself just standing in front of her 
BM would no-diff Doffy.
