In November 1999 Transcontinental Media acquired Canada's Information Technology publishing house Plesman Communications Inc, publishers of Computing Canada, CDN Computer Dealer News and Direction Informatique, among others.
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On January 29,2000, GTC Transcontinental announced its acquisition of the publishing business of Telemedia for $150 million, including Canadian Living, Homemakers, and the Canadian editions of Elle and TV Guide.
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In 2002, Transcontinental Media acquired 12 newspapers and two printing plants in Atlantic Canada and Saskatchewan from CanWest Global for $255 million, in what was one of the company's largest transactions to date.
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The Competition Bureau approved the sale in May 2014, under the condition that Transcontinental Media divest 34 of its Quebec newspapers for competition reasons.
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In March 2014, Transcontinental Media acquired US packaging supplier Capri Packaging; CEO Francois Olivier considered flexible packaging to be a diversification into a "new promising growth area", amidst softening revenue in advertising, and decreases in its core printing businesses.
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Transcontinental Media received a contract to print magazines and marketing materials for TVA through 2021.
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Transcontinental Media stated that it wanted to focus more on its local properties.
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In May 2016, Transcontinental Media sold its 13 newspapers in Saskatchewan to Star News Publishing of Alberta.
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On December 1,2016, Transcontinental Media acquired Rogers Media's financial industry publications, including Advisor's Edge, Avantages, Benefits Canada, Canadian Insurance Top Broker, Conseiller, Canadian Investment Review and the Canadian Institutional Investment Network.
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On September 19,2019, Transcontinental divested its financial industry publications between Contex Media and Newcom Media.
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Transcontinental Media established its packaging business in 2014 with the purchase of Capri Packaging, as part of a move to diversify beyond its declining print and advertising businesses.
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Transcontinental Media Printing is the largest commercial printing company in Canada, and one of the largest in North America.
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In May 2019, Transcontinental Media announced that it would close its Brampton plant by the end of 2019, resulting in the loss of 125 jobs.
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Transcontinental Media primarily published specialty business-to-business publications, particularly within the construction and financial industries.
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The former Rogers B2B publications were sold to the Toronto-based Newcom Transcontinental Media, leaving only Transcontinential's construction industry unit Groupe Constructo, and its book publishing unit.
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