I looking around the ol' metaverse when I stumbled upon PokerStars VR for free and decided to take in a tournament.
Caesar’s Palace 058/365
This one came out in December of 1992 but my December file is loaded so here ya go February, a game with the looks of Vanna White but no letter flipping. You really can't go wrong with video game gambling.
Lunar Pool 036/365
"Fuck you Minnesota Fats, You ever play Lunar Pool" was first said on February 5th, in the year of our lord 1985.
Casino Kid 006/365
When this came out on the 6th of January in 1989 I was far too young to understand the power of gambling but now I play Texas Hold 'Em on my Oculus so it would have been a good fit.