Following independent and short film roles, Sidney earned recognition with the horror series American Horror Story: Roanoke (2016). Her breakthrough came with the period drama film Fences (2016), for which she received a nomination for the Screen Actors Guild Award for Outstanding Performance by a Cast in a Motion Picture. She subsequently appeared in the biographical film Hidden Figures (2016) and the superhero film Fast Color (2018).
Sidney earned praise for leading FOX's vampire drama The Passage (2019) and playing young Venus Williams in King Richard (2021). For her performance in King Richard, she earned critical acclaim and received several accolades, such as nominations for the Black Reel Award for Best Breakthrough Performance and the Critics' Choice Movie Award for Best Young Performer.
Sidney began acting in 2012, starring in a minor role as Amity in the short horror film The Babysitters. She next made a guest appearance as Kizzy Waller in the miniseries Roots, and was soon cast in the horror television series American Horror Story: Roanoke in the recurring role of Flora Harris, which was her breakthrough role. Both were played in 2016. Sidney starred in the period drama film Fences as Raynell Maxson, and also starred in the biographical drama film Hidden Figures as Constance Johnson, both of which were released in December 2016. The films were critically acclaimed, and the former film earned her nominations for the Critics' Choice Movie Award for Best Acting Ensemble and the Screen Actors Guild Award for Outstanding Performance by a Cast in a Motion Picture.

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