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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...
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 ...
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...
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...
FIFA Soccer Manager
Windows XP/98/951997 Electronic Arts
Patrician 2: Quest for Power
Windows XP/98/952000protected ASCARON Entertainment
Big Business
DOS1990 Off The Wall Productions
Step into the gray, morally ambiguous world of corporate domination with Big Business. It’s Monopoly with fewer dice and more spreadsheets. Crush your competitors, manipulate...
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...
Ports of Call
DOS1989 International Software Development
Nomad
DOS1993 Papyrus Design Group
In Nomad, you’re a space pilot with a ship full of bad decisions and a galaxy’s worth of trouble. The game throws you into a vast star map to explore, trade, and occasi...
Capitalism Plus
DOSWindows XP/98/951997protected Enlight Software
Before there was Capitalism 2, there was Capitalism Plus, which basically took the original and added a few bells, whistles, and ways to fail spectacularly. It’s like being h...
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...
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...
Gloriana
DOS1996 ASCARON Entertainment
Gloriana sails into the realm of naval strategy with a focus on historical battles and tactical maneuvering. Ships move with a deliberate pace, and positioning is everything, turni...
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...
China Sea Trader
DOS1989
Forget piracy—China Sea Trader makes hauling porcelain and spices across 19th-century Asia feel like a cutthroat business. It’s part economic sim, part geography lesson...
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...
Space Rogue
DOS1989 Origin Systems
Space Rogue is what happens when Elite and Ultima decide to have a baby… in space. You’re dumped into a universe of hostile aliens, smugglers, and zero-g dogfights, an...
Ascii Sector
Windows Vista/7/8LinuxDOS2007freeware
Ascii Sector is what happens when someone takes Privateer, removes the graphics, and replaces them with pure ASCII and sheer willpower. It’s open-world space sim meets roguel...
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...
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
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, ...
Rags to Riches
DOS1993 Interplay Productions
Merchant Prince
DOS1993 Holistic Design
Black Monday
DOS1987 Starsoft Development
Black Monday (1987) combines economic panic with the thrill of—wait for it—spreadsheet navigation. It's like Wolf of Wall Street without the fun, drugs, or DiCaprio. Yo...
Port Royale
Windows XP/98/952002protected ASCARON Entertainment
Patrician
DOS1992protected 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...
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