Why is a pineapple on top of the Wimbledon trophy?

Answer 1

Believe it or not, it does. The Webb Ellis Cup also has an ornate head atop each of the handles. The 1906 design is based on a silver cup first fabricated in 1740, and includes the pineapple as a symbol of hospitality.

Answer 2

Pineapples were a symbol of status and wealth following their introduction. They adorn many posh antiques, and even the pillars of some stately homes.