A History of Short Words

From the New York Times Crossword Puzzle

PIP

Sun, 27 Nov '22
Gambling spot?
Sun, 23 Jan '22
Spot at a casino
Mon, 25 Oct '21
Backup singer for Gladys Knight
Wed, 28 Jul '21
Small hard seed
Sat, 5 Jun '21
Spot on a face
Thu, 29 Apr '21
Apple or orange seed