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1000+ items

Locked In Scottish Scratchcard Humour - Vintage Retro Baseball Cap

AberDons

$25.19

What Part Of Fifteen Two Fifteen Four A Pair Is Six Don't You Understand Craps Dice Game Gambler Dad Hat

PopStars1993

$28.34

Item preview, What Part Of Fifteen Two Fifteen Four A Pair Is Six Don't You Understand? Craps Player Gambler Casino Dice Game designed and sold by PopStars1993.

What Part Of Fifteen Two Fifteen Four A Pair Is Six Don't You Understand? Craps Player Gambler Casino Dice Game Dad Hat

PopStars1993

$28.34

Item preview, What Part Of Fifteen Two Fifteen Four A Pair Is Six Don't You Understand? Blackjack Card Game Player Gambling designed and sold by PopStars1993.

What Part Of Fifteen Two Fifteen Four A Pair Is Six Don't You Understand? Blackjack Card Game Player Gambling Baseball Cap

PopStars1993

$28.34

Bet You Didn't Think You Would Be This Dumb Dad Hat

VisionWind

$25.19

Bet You Didn't Think The Future Would Be This Dumb Dad Hat

VisionWind

$25.19

ORIGINAL PSG LOGO - VINTAGE 1970 Dad Hat

The Artwork

$25.19

Today's Cruise Forecast Drinking with A Chance of Gambling Dad Hat

Randomera

$27.29

I'm Not Addicted To Gambling I'm Addicted To Hope Dad Hat

Randomera

$27.29

Ace of Spades with Poker Chip Dad Hat

sneidere9dace

$23.09

Uncut Gems: This Is How I Win Baseball Cap

Art's Diner

$23.09

I Love Sports Betting Baseball Cap

Studio Sonder

$23.72

Gentleman Stallion – Sharp Dressed Horse for Race Day Dad Hat

MyxaART

$25.19

I'm Not Addicted To Gambling I'm Addicted To Hope Funny Gambler Dad Hat

RuperDelois

$26.24

watch me win! Baseball Cap

What you are is Beautiful

$25.19

Anime Inspired Character Design Bet Baseball Cap

What you are is Beautiful

$25.19

1X2 The Safe Bet Streetwear Design Baseball Cap

Spalato Originals

$25.19

Blackjack or Bust: All-In Attitude, No Safety Net Baseball Cap

Ignorant-Artist

$25.19

GAMBLER Elf Family Matching Christmas Group Dad Hat

CosmoKitsch

$25.19

Horse Racing Winner 2026 Race Day Champion Lucky Horse Design Baseball Cap

kiralynstration

$27.29

Funny Horse Racing Badge - I Chase Odds Not Dreams - Retro Betting Graphic Dad Hat

Wear Sculpt

$25.19

Derby Day Horse Racing Vintage Celebration Shirt Dad Hat

ArcaneArtistry

$25.19

152nd Derby Day Horse Racing Event 2026 Kentucky Horse Racing Fan Baseball Cap

KrystinaGiGi

$26.24

Are you the Donkey? Poker Chip - Purple Baseball Cap

SquishyKitkat

$24.35

I Have a Sports Betting Problem Funny Sarcastic Gambling Dad Hat

dudelinart

$25.19

Are you the Donkey? Poker Chip - Deep red Dad Hat

SquishyKitkat

$24.35

Texas Hold Em Casino Ring Dad Hat

HiddenLoot

$23.09

Modern Golden Solar Eclipse Online Slots Aztec Art Dad Hat

LABUTI-SHOP

$31.49

Are you the Donkey? Poker Chip - Yellow Baseball Cap

SquishyKitkat

$24.35

Are you the Donkey? Poker Chip - Blue Baseball Cap

SquishyKitkat

$24.35

Are you the Donkey? Poker Chip - GreenYellow Dad Hat

SquishyKitkat

$24.35

Are you the Donkey? Poker Chip - Green Baseball Cap

SquishyKitkat

$24.35

152nd Kentucky Derby – Horse Racing Celebration Design Baseball Cap

Combat Skies

$32.53

Poker Night Baseball Cap

DDLeach

$25.19

Casino Roulette Baseball Cap

MorningFive

$29.39

Poker Celebration Dad Hat

LewpyG

$23.72

Flaming Ace of Spades Poker Dad Hat

CamaleonDesigns

$24.98

Talk Derby To Me Shirt - Funny Horse Racing T-Shirt Dad Hat

MerchlyMike

$23.09

horse racing Girl Like A Normal Girl But Cooler Baseball Cap

GabbyKash

$25.19

Talk Derby To Me Horse Racing Fan Kentucky Derby Enthusiast Dad Hat

SofenArt

$26.24

Funny Parlay Design Always The Last Leg Dad Hat

FsqauredDesigns

$23.09

I Just Hope my Parlay Hit Sports Betting Football Tailgate Baseball Cap

DeanASkinner

$29.39

I Just Hope my Parlay Hit Sports Betting Football Tailgate Baseball Cap

DeanASkinner

$29.39

Traditional Horse Racing Jockey With Golden Horseshoe And Red Roses Illustration Baseball Cap

HarinDonreka

$26.24

Win Place Show - Black Dad Hat

LewpyG

$23.72

Win Place Show - White Baseball Cap

LewpyG

$23.72

ManBetX Sports Betting Minimalist White Logo Dad Hat

Kenalandors

$29.39

Debet Betting Site Sportswear Style Logo Baseball Cap

Kenalandors

$29.39

Betano Official Betting Sponsor Vector Logo Baseball Cap

Kenalandors

$29.39

3D Casino Poker Chip and Pair of Dice Baseball Cap

Creatby7030

$23.09

Bulldog Poker Chip Dad Hat

SquishyKitkat

$24.35

It’s Only A Problem If You’re Losing Funny Gambling Baseball Cap

tadmercado

$25.19

It’s Only a Problem If You’re Losing Funny Gambling Quote Baseball Cap

tadmercado

$25.19

It’s Only A Problem If You’re Losing Gambling Funn Baseball Cap

tadmercado

$25.19

It's Only a Problem If You're Losing Funny Gambling Meme Dad Hat

tadmercado

$25.19

I Love Texas Hold Em Dad Hat

shitpostee

$25.19

I Love Roulette Dad Hat

Thanks for the Chips! Dad Hat

SquishyKitkat

$24.35

Funny Horse Racing Work Is for People Who Can't Pick a Winner Dad Hat

jaygo

$25.19

I Love Texas Hold Em Baseball Cap

shitpostee

$25.19

All In: Three Aces and a Dollar Bill Dad Hat

artsdylan

$28.34

The Last Chip - Poker & Casino Classic Logo Dad Hat

artsdylan

$28.34

The Losing Streak - Casino Dealer Art Baseball Cap

artsdylan

$28.34

The House Always Wins - Vintage Casino Gold Chips Baseball Cap

artsdylan

$28.34

The Slow Decay of a Gambler's Life - Dark Aesthetic Dad Hat

artsdylan

$28.34

High Stakes, Deep Ruins Baseball Cap

artsdylan

$28.34

I Love Roulette Dad Hat

shitpostee

$25.19

I Love Poker Baseball Cap

shitpostee

$25.19

I’m Off to the Races! | Horse Racing Vibes | Jockey Life & Betting Humor Dad Hat

Ignorant-Artist

$25.19

Green Checks Square Baseball Cap

Talented Bum

$24.14

Green Checks Shield Baseball Cap

Talented Bum

$24.14

Parlay Sports Bettor Parlaysexual Funny Sports Betting Baseball Cap

StephanieSBeama

$29.39

Parlay sports betting Baseball Cap

StephanieSBeama

$29.39

Funny Gambling Sports Betting Parlay Can't Win Joke Baseball Cap

StephanieSBeama

$29.39

Don't be a Pig! Poker Chip Baseball Cap

SquishyKitkat

$24.35

The Parlay Made Me Do It Funny Sports Betting Shirt Dad Hat

POD DYNASTY | Original Print On Demand T-Shirt Graphics

$25.19

Bet The Over Sports Betting Quote Baseball Cap

Armendariz3

$25.19

Funny Gambling Sports Betting Parlay Can_t Win Joke Baseball Cap

JulieEldredge

$25.19

Bet The Over Sports Betting Quote Baseball Cap

LambertD9

$25.19

Fantasy Football Freak Dad Hat

Bjorkqvist

$23.09

Bet on the Blockchain - Black Text Baseball Cap

Fight The Shirts

$26.24

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