Cummings was born in Birmingham, England, in 1968. He attended the Solihull School in the West Midlands and then went on to Christ Church College at Oxford University. His choice of a musical career was cemented as he attended the Royal College of Music in London, at first focusing on the harpsichord. Among his teachers was Jill Severs. Soon, Cummings was landing continuo slots with leading early music groups in Britain and beyond, including The Sixteen, Les Arts Florissants, and the Gabrieli Consort. He made his recording debut in 1995 as a solo harpsichordist, issuing an album of suites by Louis Couperin on the Naxos label. Cummings recorded several more albums of harpsichord music on Naxos in the late '90s and early 2000s.
In the new century, Cummings became increasingly interested in conducting. His album debut as a conductor came on the BIS label in 2001, with a recording of Handel's Gloria (rediscovered only that year) and Dixit Dominus, HWV 232. Cummings has conducted both early music groups, including The English Concert, the Irish Baroque Orchestra, and the Orchestra of the Age of Enlightenment, and conventional ensembles such as the Royal Liverpool Philharmonic, the Ulster Orchestra, and the Royal Northern Sinfonia. His U.S. debut came with Boston's Handel and Haydn Society, and he has also conducted the Saint Paul Chamber Orchestra. Cummings became artistic director of Germany's Göttingen International Handel Festival in 2011. He has conducted opera at the English National Opera and the Glyndebourne Festival Opera, and many of his recordings in the 2010s, made for Accent and other labels, were of Handel operas or oratorios. From 1997 to 2012, Cummings was Head of Historical Performance at the Royal Academy of Music. He released a pair of albums in 2022, issuing a recording of Handel's opera Rodelinda, HWV 19, with the FestspielOrchester Göttingen on Accent, and backing countertenor Randall Scotting with the Orchestra of the Age of Enlightenment on The Crown: Heroic Arias for Senesino. ~ James Manheim, Rovi