A warm cloth cap worn while sleeping, often with pajamas, being common attire in northern Europe before effective home heating became widespread. From 14th c.Winston wore a nightcap to stave off the cold.
A beverage drunk before bed that is usually alcoholic. From 1818.I'll make myself a nightcap of whisky and lemon before heading to bed.
(US, sport, baseball) The final match of a sporting contest, especially the second game of a baseball doubleheader. From 1939.