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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 ...
Elite
DOS1987freeware Firebird
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, ...
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...
Uncharted Waters 2: New Horizons
DOS1995 KOEI
Uncharted Waters 2: New Horizons is an abandoned simulation game, sequel of Uncharted Waters, developed and released by KOEI in 1995. The Uncharted Waters series is set in the Age ...
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...
Uncharted Waters
DOS1990 KOEI
Pirates! Gold
DOSWindows 3.xMac OS1993protectedremakedemo 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...
Frontier: Elite 2
DOS1993 Frontier Developments
Frontier: Elite II is a classic space simulation and trading game released in 1993, developed by David Braben and his company Frontier Developments. Frontier is the sequel to the p...
Ocean Trader
DOS1995 Software 2000
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...
Wing Commander: Privateer
Windows XP/98/95DOSMac OS1993protected Origin Systems
High Seas Trader
DOS1995 Impressions Games
Ascii Sector
Windows 10/11LinuxDOS2007freeware
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...
Oil Imperium
DOS1989 reLINE Software
Elite Plus
DOS1991 Realtime Games
Elite Plus is an enhanced version of the classic space trading and combat simulator Elite, released by MicroPlay in 1991 for MS-DOS. It was designed as an update to the original 19...
Drug wars: a game based on the New York drug market
DOS1984
If you’ve ever wondered what it’s like to be a criminal economist in 1980s New York, Drug Wars has your fix—pun intended. This early DOS classic throws you into t...
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...
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...
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...
Ports of Call
DOS1989 International Software Development
Sid Meier's Pirates!
DOS1987protected MicroProse Software
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...
Iron Seed
DOS1994freeware
Released in 1994, Iron Seed is a DOS space sim that tried to be both philosophical and technical. You’re leading a fledgling human colony across the stars, tinkering with dip...
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...
Yuppi's Revenge
DOS1988 Ariolasoft
Yuppi's Revenge is what happens when ‘80s satire meets office rage. You’re a disgruntled ex-yuppie on a rampage through the corporate world—armed with a golf club...
Patrician 2: Quest for Power
Windows XP/98/952000protected ASCARON Entertainment
Machiavelli the Prince
DOS1995protected Holistic Design
Port Royale
Windows XP/98/952002protected ASCARON Entertainment
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