- Harry Christophers and a few friends leave the choir of Magdalen College, Oxford. In November, Peter Nelson (a regular at Magdalen Evensong and a fan of Tudor music) asks if Harry will put on a concert of some of his favourite pieces. The group for that concert stays together as the embryo that eventually hatches as The Sixteen.
- The choir continues in its fledgling unnamed format – members are paid £5 and a pint of beer for each concert.
- On 5 May, The Sixteen gives its first billed performance at Magdalen College Chapel, Oxford. The concert, “An Age of Innovation”, featured music by Mundy, Purcell, Pelham, Humfrey and Schütz. Ticket prices range from 70p to £1.50.
- On 12 May, The Sixteen gives its debut performance in London at St John’s, Smith Square.
- The Sixteen makes its first recording: Salve Regina, music from the Eton Choirbook, which is released on the Meridian label.
- On 27 May, The Sixteen makes its BBC debut.
- The Sixteen makes its first of 17 recordings for Hyperion Records.
- The Symphony of Harmony and Invention (now called The Orchestra of The Sixteen) is founded for the group’s first ever Messiah performance at St John’s, Smith Square. There were three further performances in this venue, and the performances were recorded live for Hyperion.
- The Sixteen performs ten Messiahs in 13 days (from London to Barcelona, back to London and then to Italy!)
- The Sixteen makes its first of seven recordings for Chandos Records.
- The Sixteen records Grand Prix du Disque - Handel Messiah and Grand Prix du Disque - Taverner Missa Gloria Tibi Trinitas on Hyperion.
- The Sixteen makes its first of five recordings for Virgin Classics.
- On 16 August, The Sixteen makes its Salzburg Festival debut.
- In December, The Sixteen tours Brazil for the first time.
- The Sixteen makes its first of 34 recordings for Collins Classics.
- On 17 August, The Sixteen makes its first appearance at the BBC Proms. The programme comprises Poulenc Figure Humaine and Bach Cantata 147.
- In October, The Sixteen tours Japan for the first time.
- In May, The Sixteen takes part in the world premiere of Sir Harrison Birtwistle’s opera Gawain at the Royal Opera House.
- On 13 November, The Sixteen films Messiah in Dublin for BBC TV.
- The Sixteen receives a Gramophone Award for "Early Music Recording of the Year" for "The Rose and the Ostrich Feather - Music from the Eton Choirbook".
- The Sixteen also receives the Diapason d'Or award for the recording of Texeira's Te Deum.
- The Sixteen also receives the Preis der Deutschen Schallplattenkritik award for the recording of Handel's Alexander's Feast.
- In April, The Sixteen tours Australia for the first time.
- The Sixteen receives the Preis der Deutschen Schallplattenkritik for the recording of Britten's "Ceremony of Carols".
- In November and December, The Sixteen tours the USA for the first time.
- On 16 November, The Sixteen makes its debut at the Mann Auditorium, Tel Aviv, in a semi-staged performance of Purcell's Fairy Queen.
- The Sixteen receives the Preis der Deutschen Schallplattenkritik for "A la Gloire de Dieu" (a recording of Stravinsky and Poulenc).
- On 24 October, The Sixteen makes its debut at the Macau Festival.
- The Sixteen receives the Preis der Deutschen Schallplattenkritik for the Frank Martin recording.
- In July, The Sixteen makes its Istanbul Festival debut.
- The Sixteen makes its debut at the Teatro São Carlos, Lisbon, with Monteverdi Il ritorno d'Ulisse in patria.
- On 1 December, The Sixteen makes its debut at the Musikverein, Vienna.
- On 30 March, The Sixteen makes its Bridgewater Hall debut with the BBC Philharmonic.
- The idea for the group’s annual Choral Pilgrimage is hatched by Anthony Smith, then president of Magdalen College and chairman of The Sixteen’s Development Board, and colleagues.
- The Sixteen initiates the Millenium project, The Choral Pilgrimage, taking Renaissance music to up to twenty cathedrals and churches around the UK. Now an annual event, it remains a unique tour of its kind in Britain.
- On 10 December, The Sixteen sings its 100th performance of Handel's Messiah at Miyahaki Arts Centre, Japan.
- On 15 December, The Sixteen makes its Tokyo Opera City debut.
- CORO, The Sixteen’s record label, is launched.
- The Sixteen becomes "The Voices of Classic FM".
- The Sixteen commissions O Bone Jesu from James MacMillan.
- In August, The Sixteen makes its debut with the Academy of St Martin in the Fields.
- CORO supplies all major digital platforms from iTunes & MSN to specialists.
- This year is The Sixteen's inaugural year at the Handel in Oxford Festival.
- The Sixteen tours nine cities in the US, performing in the New York Lincoln Center and continuing across the country as far as Los Angeles.
- This year The Sixteen makes its first of four recordings for Universal Classics.
- The Victoria Requiem CORO recording is nominated for a Midem Classical Award.
- Traditional Carols (CORO) creates classical downloads record on iTunes.
- The Sixteen also collects the Classical Brit Award for "Renaissance" at the Royal Albert Hall, in a televised event.
- The Sixteen is the first choral group to be appointed Associate Artists of the Southbank Centre.
- Eamonn Dougan is appointed as The Sixteen’s Assistant Conductor.
- The Victoria Requiem CORO recording is nominated for a Gramophone Award.
- The Sixteen features in the four-part documentary series on BBC Four, Sacred Music, presented by Simon Russell Beale. The series has since been repeated on BBC Two.
- In December, The Sixteen gives its 150th performance of Handel’s Messiah.
- The Sixteen becomes a media partner with SkyArts.
- The Sixteen celebrates its 30th anniversary with a double Choral Pilgrimage, travelling to almost 30 venues with two programmes, one including the Orchestra of The Sixteen, celebrating three composers’ anniversaries.
- In August, members of The Sixteen undertake a real pilgrimage in addition to their Choral Pilgrimage. Harry Christophers and members of The Sixteen complete a 110-mile walk from Guildford Cathedral to Canterbury Cathedral in aid of World Vision and The Canterbury Gift, raising over £12,000.