Wiles, 29, joins previously announced riders Lizzie Deignan, Elisa Longo Borghini, Lotta Lepistö, Ruth Winder, Lauretta Hanson, and Abi Van Twisk in the new project sponsored by the US bike manufacturer and run in conjunction with the Trek-Segafredo WorldTour team.
"I am incredibly excited about signing with Trek Factory Racing for 2019 and 2020," Wiles said in a statement released by the team.
"I loved working closely with Trek this year because it truly feels like a close-knit community, and that is something very unique and special about the company," she said. "The huge steps they continue to take to support women's cycling I believe will pave the way for the future of our sport. I am really proud to be a part of that movement and a member of such a power-packed team. We have an amazing roster and will be directed by two absolute legends of the sport, so I can't wait to see what we can accomplish together."
Wiles, who began her professional career in 2011 with Peanut Butter & Co-Twenty12, has also ridden for Specialized-Lululemon in 2013 and 2014, Velocio-SRAM in 2015, Orica-AIS in 2016, UnitedHealthcare in 2017 and Trek-Drops this year.
In her seven-year pro career, Wiles has taken overall wins at the 2015 Tour of New Zealand, the 2015 Cycliste Féminin International de l'Ardèche, and the 2017 Tour of the Gila as well as finishing second in the 2016 La Route de France. Wiles won a stage and the mountains classification at the Lotto Thüringen Ladies Tour last year, finishing fifth overall.
In 2018, Wiles was runner-up to UnitedHealtcare's Katie Hall at the Amgen Tour of California Women's Race, and she was 10th at the Lotto Thüringen Ladies Tour. She finished second to world champion Amber Neben at the US time trial championship and most recently was fourth overall at the Boels Ladies Tour.
The team says Wiles will be targeting a 2020 Olympic spot in the coming seasons.