A 99 Flake can refer to an ice cream cone with a Cadbury Flake inserted in it; a specially produced Flake bar for this purpose; or a wrapped ice cream cone product marketed by Cadbury. It was originally designed to be a cuboid, and fit into a wafer. It was later adapted for a cone.
99 Flake Wikipedia
A 99 Flake ice cream, or more commonly a 99 or ninety-nine, is an ice cream cone, usually made with soft serve ice cream, into which a Flake bar has been inserted. The ice cream is usually vanilla flavoured. They are sold by ice cream vans and parlours. Variations include a 99 with two flakes - often referred to as a double 99 or "bunny's ears" - and a 99 with strawberry or raspberry syrup on top, sometimes known as monkey's blood.
There are many references to 99s in British and Irish pop culture. The pop-electronica duo The KLF used ice-cream van iconography and included the phrase "Make mine a 99" in their 1991 single version of "Justified and Ancient". DI Alec Hardy eats a ninety-nine in the first episode of Broadchurch.
The Flake chocolate bar manufactured and marketed by Cadburys itself was first developed in the UK in 1920. An employee of Cadbury's noted that when the excess from the moulds used to create other chocolate bars was drained off, it fell off in a stream and created folded chocolate with flaking properties. In 1930, Cadbury started producing a smaller version of the standard Flake bar especially for ice cream cones. These were marketed under the name 99 Flake and sold loose in boxes rather than individually wrapped like the traditional Flake.
The origins of the name are uncertain. One claim is that it was coined in Portobello, Scotland when Stefano Arcari, who opened a shop in 1922 at 99 Portobello High Street, would break a large 'Flake" in half and stick it in an ice cream. The name came from the shop's address. A Cadbury representative took the idea to his company.
Another possibility, is that it was named by Italian ice-cream sellers (many from mountainous areas in the Veneto, Trentino, Bellunese, and Friuli) in honour of the final wave of conscripts from the First World War, born in 1899 and referred to as "i Ragazzi del 99" - the Boys of '99. They were held in such high esteem that some streets in Italy were named in honour of them. The chocolate flake may have reminded them of the Alpine Regiment's hat, with a long dark feather cocked at an angle.
Another claim to have invented the 99 is made by the Dunkerleys in Gorton, Manchester, with a sweet shop at 99 Wellington Street.
The Cadbury website says that the reason behind the Flake being called a 99 has been "lost in the mists of time" although it also repeats an article from an old Cadbury works paper, which states the name came from the guard of the Italian king which consisted of 99 men and "subsequently anything really special or first class was known as 99."