A History of Short Words

From the New York Times Crossword Puzzle

WIN

Fri, 11 Feb '22
Morale booster
Thu, 2 Dec '21
Success
Tue, 16 Nov '21
Earn the most votes, say
Thu, 21 Oct '21
Connect four in the game Connect Four, e.g.
Tue, 5 Oct '21
Victory
Wed, 8 Sep '21
Take home the gold
Thu, 29 Apr '21
The 1, in 1-0
Mon, 1 Feb '21
Finish first in a race