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Colosseum Treasures
This is a list of what you can bet at the Colosseum, what you win in return, and the monster that you will have to fight, in that order. I think the list is complete, and unless I've missed an item somewhere anything that's not listed here will only put you against Chupon. You can't defeat Chupon but you will not lose what you wagered.
ITEM BET ITEM WON MONSTER FOUGHT
Aegis Shield Tortoise Shield Borras
Air Anchor Zephyr Cape Brontaur
Assassin Sword Breaker Test Rider
Atma Weapon Graedus GT Behemoth
Aura Strato Rhyos
Aura Lance Sky Render Land Worm
Behemoth Suit Snow Muffler Outsider
Blizzard Ogre Nix Scullion
Blizzard Orb Rage Ring Allosaurus
Bone Club Red Jacket Test Rider
Break Blade Break Blade Lethal Weapon
Cat Hood Merit Award Hoover
Charm Bangle Dragon Horn Retainer
Chocobo Suit Moogle Suit Veteran
Coronet Regal Crown Evil Oscar
Crystal Enhancer Borras
Crystal Helm Diamond Helm Dueller
Crystal Mail Ice Shield Covert
Crystal Orb Gold Hairpin Borras
Cursed Ring Air Anchor Steriodite
Cursed Shield Cursed Ring Didalos
Czarina Gown Minerva Sky Base
Doom Darts Bone Club Opinicus
Dragon Claw Sniper Test Rider
Dragon Horn Gold Hairpin Rhyos
Drainer Drainer Enuo
Economizer Dragon Horn Vectagoyle
Elixer Rename Card Cactrot
Exp. Egg Tintinabar Steriodite
Falchion Flame Shield Outsider
Fenix Down Magicite Cactrot
Fire Knuckle Fire Knuckle Tumbleweed
Fixed Dice Fire Knuckle Trixter
Flame Sabre Ogre Nix Evil Oscar
Flame Shield Ice Shield Iron Hitman
Force Armor Force Armor Sr. Behemoth
Force Shield Thornlet Dark Force
Gauntlet Thunder Shield Vectagoyle
Gem Box Economizer Sr. Behemoth
Genji Armor Air Anchor Borras
Genji Glove Thunder Shield Hemophyte
Genji Helmet Crystal Helm Fortis
Genji Shield Thunder Shield Retainer
Gold Hairpin Dragon Horn Evil Oscar
Graedus Dirk Karkass
Hardened Murasame Phase
Heal Rod Magus Rod Pug
Hero Ring Pod Bracelet Rhyos
Ice Shield Flame Shield Flame Shield
Illumina Scimitar Scullion
Imp Halberd Cat Hood Allosaurus
Imp's Armor Toroise Sheild Rhyos
Magus Rod Strato Allosaurus
Marvel Shoes Tintinabar Tyranosaur
Megalixer Siegfried Tintinabar
Merit Award Rename Card Covert
Minerva Czarina Gown Pug
Mirage Vest Red Jacket Vectagoyle
Moogle Charm Charm Bangle Outsider
Moogle Suit Nutkin Suit Madam
Murasame Aura Borras
Muscle Belt Crystal Orb Allosaurus
Ninja Star Tack Star Chaos Dragon
Nutkin Suit Genji Armor Opinicus
Ogre Nix Soul Sabre Sr. Behemoth
Paladin Shield Force Shield Hemophyte
Pearl Lance Strato Sky Base
Pod Bracelet Hero Ring Hemophyte
Punisher Gravity Rod Opinicus
Rage Ring Blizzard Orb Allosaurus
Ragnarok Illumina Didalos
Rainbow Brush Gravity Rod Test Rider
Red Jacket Red Jacket Vectagoyle
Regal Crown Genji Glove Opinicus
Relic Ring Charm Bangle Sky Base
Rename Card Marvel Shoes Doom Dragon
Ribbon Gold Hairpin Dark Force
Rising Sun Bone Club Allosaurus
Safety Bit Dragon Horn Pug
Scimitar Ogre Nix Covert
Sky Render Aura Lance Scullion
Sneak Ring Thief's Glove Tap Dancer
Sniper Bone Club Borras
Snow Muffler Charm Bangle Retainer
Soul Sabre Falchion Opinicus
Strato Pearl Lance Aquilla
Striker Striker If not Shadow, Chupon
Stunner Strato Test Rider
Tabby Suit Chocobo Suit Vectaur
Tack Star Rising Sun Opinicus
Tao Robe Tao Robe Test Rider
Thief's Glove Dirk Harpy
Thornlet Mirage Vest Opinicus
Thunder Blade Ogre Nix Steriodite
Thunder Shield Genji Shield Outsider
Tiger Fangs Fire Knuckle Mantodea
Tintinabar Exp. Egg Dark Force
Titanium Cat Hood Brachosaur
Tortoise Shield Titanium Steriodite
Trump Trump Allosaurus
Valiant Knife Assassin Wooly
Wing Edge Sniper Rhyos