| 1 | Win 5 hands of poker | Gambler Holster |
| 2 | In Blackjack, double down and win the hand 5 times | $5, 25 Dead Eye XP |
| 3 | Win 3 games of Five Finger Fillet | Gambler Bandolier |
| 4 | Bust 1 Poker opponent out in each location (Flatneck Station, Saint Denis, Valentine) | $10, 50 Dead Eye XP |
| 5 | Win 3 rounds of Dominoes without drawing any tiles against 2 or fewer opponents | $10, 50 Dead Eye XP |
| 6 | Beat the Blackjack dealer in 2 locations (Rhodes, Van Horn) | $15, 100 Dead Eye XP |
| 7 | Beat the Five Finger Fillet player in every location (Valentine, Van Horn, Strawberry) | Gambler Gun Belt |
| 8 | Win 3 hands of Blackjack with 3 hits or more | $15, 100 Dead Eye XP |
| 9 | Win 3 games of Dominoes in a tow | $20, 150 Dead Eye XP |
| 10 | Win 3 hands of Poker in a row | Gambler Off-Hand Holster |
