Winnie the Pooh: Impulsivity with obsessive fixations, ADHD and OCD. Pooh is obsessed with honey and often goes through great lengths to get it. Also, he exhibits a strain of ADHD, the inattentive subtype, through his careless and indifferent behavior towards his peers. Lastly, Pooh's repetitive counting is an expression of his OCD.
Owl: Grandiose delusions (GD) and Dementia. He is of the firm belief that he is the wisest in the wood whilst he is actually scatterbrained and experiences memory loss alongside periods of irritability and frustration.
Rabbit: OCD. Rabbit is obsessed with keeping everything organized. This is often portrayed when he is gardening.
Christopher Robin: Schizophrenia. It is believed that all the characters in Winnie the Pooh are manifestations of his mood.
Piglet: Generalized anxiety disorder (GAD). Piglet worries - a lot. He exhibits classic signs of GAD and it is believed that the anxiety stems from a crippled self-esteem. His stuttering is also very likely a result of his anxiety.
Kanga: Social anxiety disorder. Her overprotectivess of her son, Roo, in the way she never lets Roo make his own decisions indicates her exaggerated fear for Roo's safety.
Roo: Autism spectrum disorder. He is unaware of danger in his surroundings and has an attachment to sitting in his mother's pouch.
Eeyore: Depressive disorder. Eeyore has a very bleak outlook on life and has never shown emotions such as joy or excitement.