Thanks, jmc44!
Here are your 25 calendar dates:
January 9, 2019 Kiko Calero
January 14, 2019 Steven Piscotty
January 22, 2019 Irv Ray
February 10, 2019 Lance Berkman
February 12, 2019 Chick Hafey
March 5, 2019 Sam Thompson
March 23, 2019 Johnny Logan
March 31, 2019 Marv Grissom
April 2, 2019 Don Sutton
April 7, 2019 Bobby Doerr
April 12, 2019 Addie Joss
April 24, 2019 Chipper Jones
May 24, 2019 Jack Pfiester
June 9, 2019 Jonathan Holder
July 22, 2019 Sparky Lyle
July 24, 2019 Barry Bonds
September 8, 2019 Al Demaree
September 17, 2019 Orlando Cepeda
October 6, 2019 Buck Ewing
October 17, 2019 Mordecai Brown
October 19, 2019 Brandon Looper
October 28, 2019 Mike Napoli
October 31, 2019 Mariano Rivera
November 29, 2019 Leo Cardenas
December 17, 2019 Dutch Meyer
They were picked randomly out of 365 possible dates between January 1, 2019 and December 31, 2019.