It is said that the game has existed as long as the crown-rimmed bottlecap (circa 1910).
(Dictionary of American Regional English)
skelly n [Origin unknown] NYC
1. also sklesy, scully pit, skellzies, skully. A children's sreet game; see quots.
1953 Brewster Amer. Nonsinging Games 115, Skelly [New York] - This game is usually played in the street. Each player is equipped with one "checker," a small block of wood or a falt stone. He pitches first at square 1. If his "checker" stops inside that square, he is entitled to another shot, and so on...The space separating the boxes in the inner group is called "skelly," and no player whose "checker" lands here may shoot again until some kind-hearted player knocks it out. 1967 DARE FW Addit NYC, Skully - game board chalked on sidewalk, yard square; bottle caps filled with wax must be shot to different points within the square. 1975 Ferretti Gr. Amer. Book Sidewalk Games 230, Skelly, surely the quintessential New York City street game, uses checkers - bottle caps filled with wax for weight, glass bottle tops worn smooth, brick chips, and the caps from half-gallon wine jugs as shooters...Also known as Sklesy, Scully-Pit, Tops, and Caps...he object of the game is to go from bx 1 to box 13 (in...progression...), then return the same way from 13 to 1. 2001 DARE File Bronx NYC (as of 1955), The essence of skelly was to fillip a weighted "checker" - usually a bottle-cap into which a washer had been placed and hot wax poured in - through a course of numbered boxes painted on the ground. The weight allowed one to strike the checkers of one's opponents out of the course with added force increasing your chance of completing the course and winning the game before they did. Skelly was a fixture of playground life and the Parks Department and Housing Authority would paint skelly courses on playground surfaces.
29 August 1920, New York Times, "Child Gamblers of Our Noisy Streets," by Helen Bullitt Lowry, pg. BRM3:
Year in and year out the game's the same in the Washington Square region. Little figures crouched on dirty cement pavements, knuckling inevitable beer bottle tops in the carrom-like gambling sport of the east side, called scully.
Scully, though, has this advantage over other east side games: it is independent of pennies and of charitable old gentlemen for spice - at least, so the leader of the Macdougal Street gang explains it:
"Yer see, five drug store bottle tops makes one nea beer top, and five near beer tops they makes one real beer top, and yer can buy things with them from other fellers."
They are street-made games - from what biological source no one seems to know - but each adapted, like the fins of a fish, to the element in which it has its being. Baseball has its street descendant in Cat, where a stick is batted across the truck crowded street. Pom Pom Pullaway has become Snatch the Bottle - with milk bottles used this year.
6 July 1950, New York Times, pg. 54:
The streets, barricaded to traffic, have been marked off for shuffleboard, volleyball, box ball, skelly, and other "quiet games," group games and lead-up games.
28 June 1958, New York Times, pg. 19:
P.A.L. GIVES CLASS
IN STREET GAMES
Collegians Who Will Lead
Play Project Get Insight
Into Skelly and Potsy