The grid represents a football pool betting form, where Jack Skellington has already initialed several of the boxes. The remaining answer words can be entered uniquely into the barred regions, in the indicated directions, two letters per box (like initials in a football pool grid).

The answers, all movie titles, clue football games traditionally played on Thanksgiving and New Year’s. In the case of the Thanksgiving games, the movies either feature Cowboys or Lions; for New Year’s, the games clue each of three bowl games: Sugar, Rose, and Orange.

The wingdings form an encoded list of the years in which the movies appeared, as well as the numbers for the columns of the football pool grid. (The cipher can be decoded on its own, providing additional clues to the movies—and potential backsolving possibilities for the puzzle answers—and can also be decoded as years are identified for each movie.)

Each movie therefore clues a unique football game: the Thanksgiving Cowboys or Lions game, or the New Year’s Day bowl game, for the year the movie was released.

Find the result of the indicated game to identify a winning square in the football pool. (The winning team’s score is found on the top of the grid, and the losing team’s score is found on the left side of the grid, as indicated by the letters “W” and “L” along the edges of the grid).

The bigrams in the nine indicated squares, in order, spell the answer: FOURTH QUARTER GAINS.