Business simulations (AKA tycoon or management simulations) sorted by release date

SimTower is an old Windows 3.x (1994) building and business simulation game where the player is tasked with the management of a skyscraper nonetheless. Raise floors, build apartmen...

Transport Tycoon is a business simulation game that puts the player at the head of a transport company to compete against rival companies. The player can build stations, airports, ...

Released in 1995, AIV Networks dares to ask: what if the real hero of industrialization was... logistics? Here, you’re not conquering worlds - you’re routing freight. B...

Hospital management has never been so weirdly German. In Biing!, you hire nurses based on looks, run a completely dysfunctional clinic, and try not to get arrested. It's part strat...

If Grand Theft Auto had a German uncle who worked in finance, it might look a lot like Dime City. Released in 1995 for DOS, this oddball title blends business simulation with under...

If you’ve ever wondered what baseball would look like if someone crammed the entire sport into a DOS machine and sprinkled a bit of 90s attitude on top, Epic Baseball has you...

SimTown is a city-building simulation game developed by Maxis and published by Electronic Arts. It was released in 1995 as a spin-off of the immensely popular SimCity series. Unlik...

Transport Tycoon Deluxe is a business simulation game where players take control of a transport company, competing against rivals. Players can build stations, airports, and railroa...

Ultimate Soccer Manager taps into the irresistible fantasy of running a football club without ever leaving your chair. Instead of flashy graphics, it offers spreadsheets, statistic...

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...

Catenaccio! Passion! Endless tactics! Championship Manager 2: The Italian Leagues delivers Serie A drama in spreadsheet form. You may not smell the espresso or hear the vuvuzelas, ...

Free Enterprise from 1996 is business simulation with a distinctly ’90s sense of ambition. You’re tasked with building and managing a corporate empire, juggling finance...

Ultimate Soccer Manager 2 refines the original formula, adding more depth, more leagues, and a slightly more approachable interface. It still revolves around data, decisions, and d...

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 ...

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...

The final Championship Manager to grace DOS—and what a send-off. Season 97/98 is the fan-favorite for a reason: every transfer, every injury, every last-minute goal feels lik...

Constructor is a simulation and strategy video game developed by System 3 and first released in 1997. In the game, players take on the role of a property developer with the goal of...

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...

Ah, Lula: The Sexy Empire (1997, Windows) — the game that tried to make adult business management classy and failed spectacularly. You play Lula, a buxom entrepreneur trying ...

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 ...