In preschool, Winny was notoriously injury-prone. Some of these instances include: being kidnapped and beaten multiple times, undergoing painful and invasive stomach surgery, being attacked and nearly drowned by an octopus, having her entire body set on fire, splitting her skull with a block of solid ice, and suffering traumatic bodily torture at the hands of a child predator.
At age thirteen, Winny has becoming heavily involved in alcohol and illicit drugs. She and her mother constantly clash over her drinking and use of cigarettes. Winny is currently in police custody for underage drinking and resisting arrest.
↑Revealed in the Arthur episode "D.W.'s Perfect Wish".
↑She was in preschool during the 2014-15 school year (at least), which likely means she turned 5 between August 1, 2014 and July 31, 2015 (Elwood Wiki uses those dates as a standard school cut-off range, but unique cases do exist). However, preschool is a large age range and she may have been born much earlier or later.
↑In Issue 146, Arthur joins the whites-only club at Lakewood. D.W. and Arthur share the same two parents.