A History of Short Words

From the New York Times Crossword Puzzle

NINES

Tue, 25 Feb '25
Most of 1999
Wed, 22 Jan '25
Dressed to the ___
Thu, 9 Jan '25
To the ___ (with style)
Thu, 27 Jul '23
Most of 1999
Thu, 13 Jan '22
Striped yellow balls, in pool
Sat, 16 Oct '21
Better part of 1999?
Sat, 16 Jan '21
Wild cards in "baseball" poker