On May 13, 2009, Circuit City announced it would sell its intellectual property, including its trademarks, brand name, and internet domain, to Systemax for $14 million.

[12] On January 30, 2015, Systemax announced the acquisition of the Plant Equipment Group ("PEG"), a business-to-business direct marketer of maintenance, repair and operations ("MRO") products, from TAKKT America .

[17] On September 17, 2012, the U.S. Securities and Exchange Commission (SEC) charged a former director of Systemax Inc for fraudulently reaping hundreds of thousands of dollars in undisclosed compensation between January 2006 to December 2010.

The SEC also alleged Fiorentino of stealing "several hundred thousand dollars worth of company merchandise that was used to market Systemax’s products."

[18][19] Fiorentino agreed to settle the SEC charges by paying a $65,000 fine and consenting to a permanent bar from serving as an officer or director of any publicly held company.

[22] On May 11, 2005, the company restated its results for the year 2004, following the discovery of errors in accounting for inventory at its Tiger Direct Inc. unit, an online retailer.