A History of Short Words

From the New York Times Crossword Puzzle

CUP

Tue, 1 Oct '24
1/16 of a gallon
Mon, 13 May '24
What the circled square in this grid represents, in 18-Across
Sun, 29 Oct '23
Part of a Yahtzee set
Sun, 27 Jun '21
Ice cream holder
Mon, 15 Feb '21
Saucer go-with