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Railroad Tycoon Deluxe
DOS1993 MicroProse Software
Railroad Tycoon Deluxe feels like someone took the original game, showered it with confetti, tuned the engine, and handed it back with a wink. Better colors, refined scenarios, and...
Uncharted Waters
DOS1990 KOEI
Uncharted Waters invites you to sail the high seas in 1990, back when exploration meant patience, curiosity, and occasionally getting very lost. This isn’t a game that rushes you...
Black Gold
DOS1991 Starbyte Software
In Black Gold (1989), you're in the cutthroat world of oil barons. It’s like Dallas, but with more charts and fewer cowboy hats. You build rigs, negotiate deals, and try to o...
Uncharted Waters 2: New Horizons
DOS1995 KOEI
Uncharted Waters 2: New Horizons takes everything its predecessor attempted and refines it into something richer and more engaging. Released in 1995, it expands the scope with mult...
Entrepreneur
Windows XP/98/951997 Stardock Entertainment
If you’ve ever dreamed of becoming a ruthless tycoon without being yelled at by shareholders, Entrepreneur (1997, Windows) is your playground. It throws you into a fierce wor...
Oil Barons
DOS1992 Starsoft Development
Oil Barons takes the glamorous world of oil speculation—yes, glamorous—and turns it into a strategy game that feels like Monopoly went through a midlife crisis. Release...
Dope Wars
Windows XP/98/951998 Beermat Software
Dope Wars is a text-based simulation game that originated as a DOS program in the early 1980s, but gained popularity in its Windows version released in 1998. The game puts players ...
High Seas Trader
DOS1995 Impressions Games
High Seas Trader offers a blend of trading and exploration that feels both relaxing and quietly strategic. You navigate the seas, making deals and managing resources, all while try...
Elite
DOS1987freeware Firebird
Elite isn’t just a game; it’s a lifestyle choice. This 1987 DOS version throws you into a vast, uncaring galaxy and says, “Good luck.” There’s trading...
Frontier: First Encounters
DOS1995 Frontier Developments
If Frontier: Elite 2 opened the door to a vast universe, Frontier: First Encounters in 1995 basically kicked it wide open and invited you to wander in. This sequel expands the form...
Elite Plus
DOS1991 Realtime Games
Elite Plus takes everything intimidating about Elite and polishes it just enough to feel slightly less hostile. The visuals are improved, the interface smoother, but the soul remai...
FIFA Soccer Manager
Windows XP/98/951997 Electronic Arts
Corporate Raider: The Pirate of Wall Street
DOS1988protected SoftServ
In Corporate Raider: The Pirate of Wall Street, you’re not sailing the high seas—you’re sinking companies from the comfort of an office chair. This business simul...
Business Simulator
DOS1987 Reality Development
Do you find spreadsheets thrilling? Does the idea of profit margins make your heart race? Then Business Simulator is your kind of party. It’s all about running a faceless com...
Oil Imperium
DOS1989 reLINE Software
If Oil Barons is Monopoly with attitude, Oil Imperium is its slightly more serious cousin who read a business textbook once and won’t let you forget it. Released in 1989, thi...
Sid Meier's Pirates!
DOS1987protected MicroProse Software
Ports of Call
DOS1989 International Software Development
Rags to Riches
DOS1993 Interplay Productions
Pirates! Gold
DOSWindows 3.xMac OS1993protecteddemo MicroProse Software
Pirates! Gold is an open world game designed by Paul Murphy, developed and released by MicroProse Software in 1993 for DOS, Windows 3.x, Mac and also Sega Genesis and Amiga CD32.&n...
Capitalism 2
Windows XP/98/95Mac OS2001protected Ensemble Studios
If spreadsheets are your love language, Capitalism 2 is pure romance. This brutally detailed simulation lets you create your own corporate empire from scratch—manufacturing, ...
Patrician 2: Quest for Power
Windows XP/98/952000protected ASCARON Entertainment
Railroad Tycoon
DOSMac OS1990freeware MicroProse Software
If you’ve ever wondered what it feels like to run a railway empire without getting coal dust all over your clothes, Railroad Tycoon is the place to start. This 1990 classic h...
Cutthroats: Terror on the High Seas
DOS1999 Hothouse Creations
1869
DOS1992 Max Design
If you’ve ever dreamed of becoming a 19th-century merchant sailing the high seas with a suspiciously optimistic outlook on international trade, 1869 is your jam. It throws yo...
Baseball Mogul
Windows XP/98/951997 Infinite Monkey Systems
Baseball Mogul (1997) was the original release that kicked off the whole franchise. Developed by Clay Dreslough and published by Infinite Monkey Systems, this was a pioneer in the ...
Merchant Prince
DOS1993 Holistic Design
Frontier: Elite 2
DOS1993 Frontier Developments
Few games capture the feeling of “the galaxy is huge and you are spectacularly insignificant” quite like Frontier: Elite 2. Released in 1993, this ambitious sequel thro...
Zeppelin: Giants of the Sky
DOS1995 Ikarion Software
Ever dreamed of running a transatlantic zeppelin empire during the golden age of flight? Zeppelin: Giants of the Sky lets you do just that — and it’s every bit as niche...
Ocean Trader
DOS1995 Software 2000
Seven Cities of Gold (Commemorative Edition)
DOS1993protected Ozark Softscape
Released in 1993, Seven Cities of Gold (Commemorative Edition) invited players to explore the New World with a mixture of discovery, strategy and occasional greed. Sailing into unk...






























