Gambling in 5th Edition D&D 3 of 7: Chess

Originally I made Chess be a competitive game, as you can see from my videos. First I will share the new rules which are based on playing 2 or 3 games against someone or a group of someones.

Chess

This is not a bet on a single Match, but instead spending 4 hours gambling on Chess. This does not count as resting.

Copper: +0 DC
Silver: +5 DC
Gold: +10 DC
100+ Gold: +20 DC

Every game will start with a Chess proficiency roll. This roll is your current score

Do Wisdom (Insight and Chess) in one roll.
DC 11: Add your Wisdom Modifier to your History Check
DC 14: You get advantage on your future Chess checks this Session
DC 17: Double your Chess proficiency on all future checks in this session

Do an Intelligence (History and Chess) check in one roll:
DC 15 Total Gambling DC -4
DC 19 Total Gambling DC -8

Do an Intelligence (Investigation and Chess) check in one roll.
Add this result to your current score.

Total score: 1d20+Chess + 1d20+Investigation + Intelligence + Chess
DC 21 You retain half of your initial bet. You won some, you lost more, but you survived
DC 25 You won some, you lost a bit more. You retain three quarters of your initial bet.
DC 29 You won some, you lost some. You break even keeping all of your money
DC 33 You won some, You lost less. You keep your money and make 50% more as well
DC 37 You lost some, you won more. You double your money.
DC 41 You won, what am I talking about, of course you won. Triple up your initial money
DC 45:. Quadruple your money.

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Those are the rules for four hours of gambling with chess. I also wanted to present a guideline for single player chess against each other.

Chess - Single Match Option
Chess is a game of strategy and foresight. Chess involves two people playing against each other. Each chess game lasts 2 hours. These games involve betting by the piece, not by a winner take all.

The standard NPC has competitor will have +1 to wisdom and +1 to intelligence and will have proficiency in 1d4 of the following skills: Chess, History, Investigation, and Insight. Roll 1 d20 for each skill the highest roll gets proficiency first, lowest last

Copper +2 Proficiency
Silver +3 Proficiency
Gold +4 Proficiency
100+ Gold +6 Proficiency

Every game will start with a competitive Chess proficiency roll. This roll is your current score

Do a Wisdom (Insight & Chess) Check
DC 13: Add your Wisdom Modifier to your History Check
DC 19: You get advantage on your future Chess checks this Session
DC 25: Double your Chess proficiency on all future checks in this session

Next, everyone proficient rolls an Intelligence (History & Chess)
DC 16: +4 To your competitive score
DC 23: +8 To your competitive score
DC 30: +12 To your competitive score

Both players make a competitive Intelligence (Investigation & Chess) check.
Add this result to your current score.

Total score: 1d20+Chess, 1d20+Investigation + Intelligence + Chess
Total score is competitive so it will be compared to your opponent's score.

DC -16 You were destroyed. You lose everything.
DC -12 You lost, more's the pity. You retain one quarter (25%) of your initial bet
DC -8 You won some, you lost more, but you survived. You retain half (50%) of your initial bet
DC -4 You won some, you lost a bit more. You retain three quarters (75%) of your initial bet.
DC 0 You won some, you lost some. You break even keeping all of your money
DC 4 You won some, You lost less. You keep your money and make 25%
DC 8 You lost some, you won more. You keep your money and make 50%
DC 12 You won, what am I talking about, of course you won. You keep your money and make 75%
DC 16 Hello Bobby Fisher. Double your money.