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Another guess: Braveland Wizard
Catacombs Pack
paper sorcerer
Round 2 Guess 9

Dungeon Keeper 2
Getting pretty deep into the WL: Depths of Peril
Alpha list update. Hopefully someone wins soon - up to 166 entries!

ZFR's latest guess of Dangerous Dave was a repeat - Bouchart had an entry for same in Rd 2 way back at bottom of page 5 (if set to show 20 posts/page). Otherwise no clear repeats yet.

1nsane
Act of War: Gold Edition
Age of Wonders: Shadow Magic
Age of Wonders 3
Airline Tycoon Deluxe
ALAN WAKE'S AMERICAN NIGHTMARE
Albedo: Eyes from Outer Space
Amnesia: The Dark Descent
Another World
Assassin's Creed®: Director's Cut.
Avernum: The Complete Saga
Bad Mojo
Baldur's Gate: Enhanced Edition
BALDUR'S GATE 2 ENHANCED EDITION
Banished.
Bard's Tale
Bastion
Battle Isle Platinum
Battle Worlds Kronos
Betrayal at Krondor
Blackwell Bundle
Blake Stone
Blocks that matter
Bloodrayne
Braveland Wizard
Broken Sword 5 The Serpents Curse
Cannon Fodder!
Caribbean
Catacombs Pack
Chroma Squad
COGNITION: GAME OF THE YEAR EDITION
Cossacks Anthology
Costume Quest
Crusader: No Regret
Crusader: No Remorse
Cyberia
Dangerous Dave Pack (dupl)
Deadnaut
Death to Spies
Depths of Peril
Descent 1+2
descent 3 + mercenary
Deus Ex GOTY
Divine Divinity
Divinity: Original Sin
Dracula Trilogy
DREAMFALL CHAPTERS SEASON PASS - SPECIAL EDITION
D&D Dragonshard
Dungeon Keeper 2
Dustforce
Eador
Earth 2140 Trilogy
Earth 2150 Trilogy
Earthworm Jim 3D
Empire Earth Gold Edition
Eschalon book I
Europa Universalis II
Europa Universalis: Rome Gold
Fall, The
Far Cry
F.E.A.R. Platinum
F.E.A.R. 2: Project Origin + Reborn
Freedom Planet
Gabriel Knight 3: Blood of the Sacred, Blood of the Damned
Geneforge Saga
Gex
ghost master
Golden Wake, A
Gothic
Gray matter
Guilty Gear X2 #Reload
Gurumin: A Monstrous Adventure
Halfway
Hasbro D&D bundle
Hatoful Boyfriend
Heroes of Might and Magic IV
Heroes Of Might And Magic 5 Bundle
Hotline Miami
ICEWIND DALE: ENHANCED EDITION
ICEWIND DALE 2 COMPLETE
Imperialism 2: The Age of Exploration
Incredible Machine Mega Pack
Independence War Deluxe

Inherit the Earth
inner world
(1nsane)
Jagged Alliance 2
Kentucky Route Zero Season Pass
King's Bounty - Dark Side
kings quest 7-8
Lands of Lore 1+2
Last Express
Legend of Kyrandia
LEGO: Batman
Leisure Suit Larry Winner 2 (of 3?)
Loom
Majesty Gold HD
majesty 2 col
Marvelous Miss Take
Massive Assault
massive assault phantom renaissance
Master of Orion 1 + 2
Mdk
mdk 2
Memoria
Men of War: Red Tide
meridian
Messiah?
Might and Magic® 6-pack
Mortal Kombat 1+2+3
Mount & Blade
Mousecraft
Myst
Neverwinter Nights Diamond Edition
Night of the Rabbit
Nox
Overlord + Raising Hell.
paper sorcerer
Pilot Brothers
Prince of Persia
Quest for Glory
Rayman 2: The Great Escape
Redneck Rampage
REVOLVER360 RE:ACTOR
Risen
Rogue Legacy
Sacred Gold
Sacred 2 Gold
Sea Dogs
Settlers® 2: 10th Anniversary, The
Shadowgate: Special Edition
Shadowgrounds Survivor
Shadowrun Dragonfall
Shovel Knight
SimCity 2000
Sokobond
Space Quest 4+5+6
S.T.A.L.K.E.R.: Call of Pripyat.
Star Wars: Jedi Knight - Dark Forces 2
Star Wars: Knights of the Old Republic
Star Wars: Republic Commandos
Sunless Sea
System Shock 2
Tales of Maj'eyal
Tex Murphy: Tesla Effect
This War of Mine
Tomb Raider 1+2+3
Toonstruck
Total Annihilation Commander Pack
Transistor
Ultima 4-5-6
Ultima Underworld 1+2
Unrest
Urban Chaos
Wing Commander 1+2
Wing Commander: Armada
Wings remastered.
Wings of Prey: Special Edition
Witcher: Enhanced Edition
Witcher Adventure Game
Wizardry 6+7
Ys I & II Chronicles+
Y's Origins
Zak McKraken and the Alien Mindbenders
Zork Anthology
Wow. Completely forgot to congratulate okkkkerlo on winning half of round #2. Congratulations, okkkkerlo.
Round #2, Guess #14: Hearts of Iron II: Complete
my next guess is Avadon: The Black Fortress
R2 guess #7: Risen 2: Dark Waters.

Also, the list has been updated.

(Many thanks to mrkgnao for creating MaGog search engine.)
Castles 1+2
avatar
bler144: Alpha list update. Hopefully someone wins soon - up to 166 entries!

Act of War: Gold Edition
Age of Wonders: Shadow Magic
Age of Wonders 3
Airline Tycoon Deluxe
ALAN WAKE'S AMERICAN NIGHTMARE
Albedo: Eyes from Outer Space
Amnesia: The Dark Descent
Another World
Assassin's Creed®: Director's Cut.
Avernum: The Complete Saga
Bad Mojo
Baldur's Gate: Enhanced Edition
BALDUR'S GATE 2 ENHANCED EDITION
Banished.
Bard's Tale
Bastion
Battle Isle Platinum
Battle Worlds Kronos
Betrayal at Krondor
Blackwell Bundle
Blake Stone
Blocks that matter
Bloodrayne
Braveland Wizard
Broken Sword 5 The Serpents Curse
Cannon Fodder!
Caribbean
Catacombs Pack
Chroma Squad
COGNITION: GAME OF THE YEAR EDITION
Cossacks Anthology
Costume Quest
Crusader: No Regret
Crusader: No Remorse
Cyberia
And, no, not yet. The key is still in play... seems to the logical counterbalance of the quick win in round 1...

Another 24 hours and we move to the 3rd round, with no less than 3 new keys entering the arena...
oddworld stranger's wrath
Phantasmagoria
Doorkickers

thanks a lot bler144 for the lists!
Shadow Warrior (2013)