He joined Glyndebourne Touring Opera in 1992, singing the role of The Madhouse Keeper in Stravinsky's The Rake's Progress, a role he repeated with Glyndebourne Festival in 1994. On the 1994 GTO tour, he created the roles of The Monstrous Messenger and Joe Shady in Sir Harrison Birtwistle's The Second Mrs Kong for which he received the GTO/Esso Award for outstanding young singers, and he subsequently repeated the roles in the 1995 Glyndebourne Festival. Other Glyndebourne Festival engagements have included Stage Hand in a new production of Janàcek's The Makropoulos Case, which has been filmed for TV and video, and which he also sang at the BBC Proms and toured to New York, Antonio/The Marriage of Figaro, Graf Lamoral in Arabella, Major Domo and La Roche (cover) in Capriccio, Quince in A Midsummer Night's Dream, Valens (Theodora), Don Fernando (Fidelio) and Christus Bach St Matthew Passion. For Glyndebourne on Tour he has sung Colline/La Bohème, Publio/La Clemenza di Tito , Valens, Don Magnifico/Cenerentola and Don Alfonso/Così fan tutte. He made his Royal Opera debut singing Fiorello/Il barbiere di Siviglia and returned for Sacristan/Tosca (and again in 2002 with Pavarotti!), most recently he has sung Zuniga / Carmen. For Opera North he covered he has sung the title role of Falstaff, First Workman Wozzeck, Colline, Sacristan, Police Commissar Der Rosenkavalier, Geronimo/The Secret Marriage, Cyrus/Croesus (by Keiser), Frère Laurent/Roméo et Juliette and Bottom/A Midsummer Night’s Dream. For Welsh National Opera he has sung Count Horn/Un ballo in maschera, Don Basilio/Il barbiere di Siviglia, Bartolo/Le nozze di Figaro and First Nazarene/Salome. For English National Opera he has sung Trojan Soldier/The Trojans, Pallante/Agrippina and Farasmene / Radamisto. He made his debut at La Monnaie in Brussels singing Soligni/Three Sisters (by Peter Eotvos) in the 2001/02 season and has returned to sing Plutone/Orfeo, Brander/La damnation de Faust, Dieu infernale and Oracle in Alceste, and Quince. He has also sung Quince for the Liceu in Barcelona and the Teatro Real in Madrid. For Garsington Opera he has sung Buralicchio in L'equivoco stravagante by Rossini and Don Magnifico. For Grange Park Opera he sang Leporello/Don Giovanni. Other roles include Banquo/Macbeth, Tutor/Le Comte Ory, Kichiga/Tchaikovsky's The Enchantress, Farlaf/Glinka's Russlan and Ludmilla, and Haly/L'Italiana in Algeri.
Henry Waddington’s concert performances of operas have included Vaughan Williams' Sir John in Love with British Youth Opera, Keeper of the Madhouse/The Rake's Progress with the BBC Symphony Orchestra, conducted by Andrew Davis at the Royal Festival, and Callestene/Poliuto and Oroe/Semiramide for the Chelsea Opera Group in London.
Concert repertoire includes the Mozart Mass in C for the Salzburg Festival and Ivor Bolton, Brander/La damnation de Faust for the Philharmonia under Charles Dutoit, Puccini Messe di Gloria for the BBC National Orchestra of Wales at St David’s Hall, Cardiff, a tour of Handel’s Solomon with the Orchestra of the Age of Enlightenment under René Jacobs including concerts in London, Paris and New York, and Handel Israel in Egypt with the Scottish Chamber Orchestra and Emmanuelle Haïm at the 2008 Edinburgh International Festival. He has performed Kurt Weill’s The Firebrand of Florence with the BBC Symphony Orchestra under Sir Andrew Davis, as well as a concert and recording of Getty's Plump Jack at St John's Smith Square. In 2008/09 he sang Messiah with the Philharmonia and also with the English Concert and Harry Bicket and the Huddersfield Choral Society. He made his Wigmore Hall debut in January 2007 singing Haydn arias with the Classical Opera Company and recently performed Haydn Seven Last Words at the 2009 Edinburgh Festival.
Recent and future operatic engagements include Jupiter/Castor and Pollux, Sacristan / Tosca and Lt. Ratcliffe/Billy Budd for English National Opera, Spinellocchio / Gianni Schicci for Royal Opera House, Covent Garden, Bartolo/Figaro for Welsh National Opera, Lt. Ratcliffe for Netherlands Opera, Pallante for the Gran Teatre del Liceu, Barcelona, Kothner / Die Meistersinger for Glyndebourne Festival Opera, Publio/La clemenza di Tito, Lodovico/Otello and Bottom/A Midsummer Night’s Dream for Opera North, Swallow/Peter Grimes for Aldeburgh Festival, as well as concert performances of Wozzeck with the Philharmonia Orchestra under Esa Pekka Salonen in Europe and the US. Concert engagements include Berlioz L’Enfance du Christ with BBC National Orchestra of Wales and Bach St Matthew Passion with Aberdeen Bach Choir.