Bolo was created by Stuart Cheshire. It began as a little-known tank game on the BBC Micro and was reborn on the Macintosh as a 16-player graphical, networked, real-time tank battle. It found a devoted following — people played 12-hour games with 16 players working in teams across networked computers around offices and university campuses. What started as an arcade shoot-'em-up became, for serious players, a deep strategy game. As Cheshire put it: "You have to play it to understand."

The Mac was Bolo's home, but Windows and Linux players had no way to join in. In 1998, John Morrison set out to change that, reimplementing Bolo from scratch for Windows as WinBolo, with a matching Linux server (LinBolo). Stuart Cheshire gave the project his blessing, and the first public release followed in 1999 as shareware under a commercial arrangement. WinBolo and the original Mac Bolo were not network compatible, and a Linux client version was also briefly available. Over the next nine years sixteen major releases followed, adding localisation, customisable skins, built-in server hosting, and game logging with a full replay viewer. Version 1.16, released in 2009, became the long-serving classic release.

The idea for WinBolo.net came around in the middle of 2000, but it took a year before any work began. It started as a way to publish the results of the #winbolo IRC server game bot to the web and to display player ranks. Almost three years after the first idea, in 2003, WinBolo.net launched properly: players could sign up and share a single online profile between the game and the community, with rankings updated automatically from the games they played — and, importantly, with no impact on the game itself, since taking part was entirely optional.

The ranking system drew on the same ELO algorithm used by chess players and by the original Internet Bolo League, adapted for WinBolo's 1v1 and team games.

In 2009, with version 1.16, the WinBolo classic version was open sourced by John Morrison under the GPL v2. The community went on to release one further version, 1.17.

Decades on, WinBolo has been rebuilt from a single shared codebase. WinBolo 2.0 brings Windows, Mac, Linux, Steam Deck, iOS, Android and Web players onto the same servers, with an authoritative server and modern netcode, high-resolution graphics, 40+ Steam achievements, Lua-scripted AI brains with a machine-learning training environment, a full map editor with procedural generators, and an embedded log viewer wired into WinBolo.net. The game remains free and open source under the GPL v2.