Sort by:
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 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 ...
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, ...
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...
Uncharted Waters
DOS1990 KOEI
Oil Imperium
DOS1989 reLINE Software
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...
High Seas Trader
DOS1995 Impressions Games
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...
Ports of Call
DOS1989 International Software Development
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...
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...
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...
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...
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...
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...
Ocean Trader
DOS1995 Software 2000
Wing Commander: Privateer
Windows XP/98/95DOSMac OS1993protected Origin Systems
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...
Taipan for Windows
Windows XP/98/952002freeware
In Taipan for Windows, you’re not a hero, you’re a 19th-century capitalist trying to get rich trading tea, silk, and the occasional bit of opium in the South China Sea....
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...
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...
Sid Meier's Pirates!
DOS1987protected MicroProse Software
Patrician 2: Quest for Power
Windows XP/98/952000protected ASCARON Entertainment
Gloriana
DOS1996 ASCARON Entertainment
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
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...
- 1
- 2






























