Games involving some sort of trading practice sorted by release date

If buying and selling goods is your thing, give these games a try. Every one of them involve trading in some form: buying and selling goods and moving them by sea (Ports of Call), stock exchange (Acquire, Black Monday), smuggling items in deep space (Elite, Frontier).

Most popular trading applications

Railroad Tycoon

simulationDOS, Mac

Capitalism 2

simulationWindows XP/98/95, Mac

Uncharted Waters 2: New Horizons

simulationDOS

Trading applications

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Railroad Tycoon Deluxe

DOS19934.1/5 MicroProse Software
Seven Cities of Gold (Commemorative Edition)

DOS1993protected4/5 Ozark Softscape
Wing Commander: Privateer

Windows XP/98/95DOSMac1993protected4.1/5 Origin Systems
Iron Seed

DOS1994freeware3.8/5
Frontier: First Encounters

DOS19954.1/5 Frontier Developments
High Seas Trader

DOS19954/5 Impressions Games
Machiavelli the Prince

DOS1995protected4.1/5 Holistic Design
Ocean Trader

DOS19954.1/5 Software 2000
Uncharted Waters 2: New Horizons

DOS19954.2/5 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 of Discovery and gives the player the freedom to set sail with their ship and go wherever you want exploring, fighting, trading, privateering, etc.
Zeppelin: Giants of the Sky

DOS19953.8/5 Ikarion Software
Gloriana

DOS19964.3/5 ASCARON Entertainment
Baseball Mogul

Windows XP/98/9519973.7/5 Infinite Monkey Systems
Capitalism Plus

DOSWindows XP/98/951997protected4.2/5 Enlight Software
Entrepreneur

Windows XP/98/9519974.1/5 Stardock Entertainment
Patrician 2: Quest for Power

Windows XP/98/952000protected4.1/5 ASCARON Entertainment
Capitalism 2

Windows XP/98/95Mac2001protected4.3/5 Ensemble Studios

Capitalism 2 is simulation game designed by Trevor Chan, developed by Ensemble Studios and released by UBI Soft in 2001 for Windows and Macintosh. Capitalism 2 is the quintessential capitalistic simulation and involves stock exchange, business management, marketing, etc.
Port Royale

Windows XP/98/952002protected4.4/5 ASCARON Entertainment
Taipan for Windows

Windows XP/98/952002freeware3.5/5
Ascii Sector

WindowsLinuxDOS2007freeware4/5