Headlands was founded in July 2009 by three former senior executives from the trading side of the Citadel Group.

At the same time, Jason Lehman was head of Citadel's global options business, and Neil Fitzpatrick was chief operating officer of Citadel Execution Services.

[2][3][4][5] In 2013, Headlands Tech Global Markets LLC was established to trade Fixed income securities.

In 2014, it started trading municipal bonds and focused mostly on lots of $100,000 or less.

[5][6] In March 2021, Toronto-Dominion Bank agreed to buy Headlands Tech Global Markets LLC from Headlands to improve its automated fixed-income trading platform.