| Year/s | Event |
|---|---|
| 1584 | Uppingham School Founded by Archdeacon Robert Johnson. The original school room built near the churchyard in Uppingham |
| 1584-1588 | David Black, Headmaster |
| 1587 | The Foundation Charter granted (now hangs in the Kendall Room) |
| 1588-1592 | George Daniell, Headmaster |
| 1592 | The Hospital built, now houses the School Library |
| 1592-1605 | William Pickering, Headmaster |
| Year/s | Event |
|---|---|
| 1602 | Henry Ferne, first known Uppingham School Boy, becomes Chaplain to Charles I |
| 1605-1614 | The Revd Ishmael Borough, Headmaster |
| 1614-1631 | The Revd John Clarke, Headmaster |
| 1631-1641 | The Revd Ezekial Johnson, Headmaster |
| 1641-1669 | The Revd Francis Meres, Headmaster: 30 plus boys now attend the School |
| 1643 | First record of decisions made by School Governors |
| 1669-1684 | The Revd Thomas Stockman, Headmaster |
| Year/s | Event |
|---|---|
| 1721-1734 | The Revd Ambrose Reddall, Headmaster |
| 1734-1747 | The Revd William Hubbard, Headmaster |
| 1747-1756 | The Revd Henry Laybourn, Headmaster |
| 1757-1771 | The Revd Henry Knapp, Headmaster |
| 1771-1777 | The Revd John Fancourt, Headmaster |
| 1777-1793 | The Revd Jeremiah Jackson, Headmaster |
| 1783 | First Old School House Studies |
| 1793-1822 | The Revd John Butt, Headmaster |
| Year/s | Event |
|---|---|
| 1811-1824 | The Revd Thomas Roberts, Headmaster |
| 1815 | First recorded cricket match against Oakham School |
| 1824-1839 | The Revd Josiah Rowles Buckland, Headmaster |
| 1827 | ‘The Upper’ is rented as 1st XI cricket field for the first time |
| 1839-1845 | The Revd George Ash Butterton, Headmaster |
| 1845-1853 | The Revd Henry Holden, Headmaster |
| 1846 | First mention of Praepostors in school literature |
| 1848 | School seal first used |
| 1848 | Railway comes to Manton |
| 1851 | The Hospitaller (first School Magazine) published |
| 1852 | First OU Cricket Match |
| 1853 | The first Lodge (boarding house) accepts pupils |
| 1853-1887 | Rev Edward Thring Headmaster, transformed the school in his 34 years of leadership |
| 1855 | First Music Master appointed First Cricket match against Oundle School |
| 1856 | First School Songs introduced Lorne House opens |
| 1857 | Uppingham Football rules established |
| 1859 | West Deyne opens Old Constables opens Athletics introduced as a sport First gymnasium in an English School |
| 1860 | Bathing place (i.e. first swimming pool) |
| 1861 | Brooklands opens |
| 1863 | Highfield(s) opens, the ‘s’ dropped after 1888 Old School Room (OSR) built Uppingham Rovers (OU Cricketers) play their first match |
| 1864 | First inter-house games cups First cricket pavilion built on The Upper |
| 1865 | The Chapel consecrated Paul David appointed as first Music and Choir Master - now known as Director of Music – the first appointment of its kind at any school |
| 1866 | West Bank opens |
| 1868 | The Lower School completed - now The Lodge (boarding house) |
| 1869 | First Headmasters’ Conference held by Edward Thring at Uppingham |
| 1871 | Fircroft opens |
| 1872-1940 | Redgate opens (closed in 1940) |
| 1872 | First Music School established |
| 1875-1877 | School transfers temporarily to Borth, Wales, due to Typhoid epidemic in Uppingham |
| 1877 | The Leicester Playing Fields are created |
| 1883 | Swimming Pool opens (a first for any school in the country) |
| 1888-1907 | The Revd Edward Carus Selwyn, Headmaster |
| 1889 | Rugby code for football adopted Uppingham School Rifle Volunteer Corp (CCF) started Galilee Chapel to house Brock's statue of Thring |
| 1890 | The present School House opens |
| 1891-1992 | The Hall (boarding house) opens (closed in 1992) |
| 1894 | The railway comes to Uppingham |
| 1895 | Meadhurst boarding house opens The Routh Cup (for cross-country) first awarded |
| 1896 | Farleigh opens |
| 1897 | The Tower (Victoria Block) built |
| 1898 | First rugby match against another school - Rugby |
| Year/s | Event |
|---|---|
| 1905 | The Boer War and Paul David Memorial Concert Hall and Gymnasium (now The Theatre) opens |
| 1908-1915 | The Revd Harry Ward McKenzie, Headmaster |
| 1910 | The Old Music School completed |
| 1914 | The Middle Playing Fields purchased |
| 1915 | The Chapel Organ installed (extensively refurbished in 1965) |
| 1916-1934 | The most Revd Reginald Herbert Owen, Headmaster |
| 1919 | The (original) Lodge (The Lower School) moves to Nevill Holt, and is no longer an integral part of Uppingham School |
| 1921 | The First World War Memorial Shrine in the Chapel is dedicated |
| 1923-1929 | East Block classrooms and Memorial Hall built |
| 1923 | Second Cricket Pavilion on The Upper built |
| 1926 | Scheme for the School to purchase the boarding houses from individual Housemasters is established |
| 1928 | Constables opens |
| 1928-1929 | Masons’ Lawn laid and Masons’ Gate erected |
| 1929 | The Leicester Pavilion completed |
| 1931 | The Memorial Hall organ installed |
| 1934-1944 | John Frederick Wolfenden (Lord Wolfenden), Headmaster |
| 1935 | The Sanatorium opens (combining Woodfield Sanatorium and Fairfield Isolation block) |
| 1939-1946 | Kingswood School shares the facilities at Uppingham throughout WWII |
| 1940 | Redgate closed |
| 1944-1965 | Martin Lloyd, Headmaster |
| 1950 | WWII Memorial and new Library opens |
| 1957 | The New Science Block completed |
| 1964 | School Shop opens for business |
| 1965 | Chapel Extension built to accommodate growing numbers at the School The Thring Centre opens and houses the Design andTechnology Department |
| 1965-1974 | John Caress Royds, Headmaster |
| 1969 | Memorial Hall divided horizontally to accommodate two floors Community Service starts (known as the Pioneer Group or Public Service for the first few years) |
| 1970 | Sports Centre built |
| 1972 | Theatre opens The Headmaster ceases to be Housemaster of School House |
| 1975-1982 | Coll MacDonald, Headmaster |
| 1975 | Fairfield opens as Uppingham’s first Sixth Form girls’ house |
| 1981 | New Music School and Buttery open |
| 1982-1991 | Nicholas Raymond Bomford, Headmaster |
| 1984 | Quatercentenary celebrations; The Queen visits |
| 1986 | Johnson's, Uppingham’s second Sixth Form girls’ house, opens |
| 1989 | Maths Block constructed |
| 1991 | Lee Astro laid to provide an all weather sport surface |
| 1991-2006 | Stephen Charles Winkley, Headmaster |
| 1993 | The Lodge opens as a Sixth Form boys' house |
| 1994 | The Lodge becomes a Sixth Form girls' house Woodfield opens as a new Lower School for entry at 11+ |
| 1995 | The Leonardo Centre opens to house Art, Design and Technology |
| 1997 | Thring Centre becomes the Sixth Form Centre |
| 1998 | Arboretum (between Spring Back Way and The Middle Playing Fields) established |
| Year/s | Event |
|---|---|
| 2001 | Sunley Astro, Uppingham’s second all weather sport surface, laid Samworths' opens as Uppingham’s first 13+ girls’ house |
| 2002 | Fairfield becomes a 13+ girls’ house |
| 2003 | The Languages Centre opens |
| 2004 | New House opens as a 13+ girls’ house |
| 2005 | The Chapel is re-ordered |
| 2006 | The Paul David Music School is completed Constables becomes a 13+ girls’ house (having been a boys’ house since 1928) The Williams Studio Theatre opens The Middle Pavilion completed |
| 2006-2016 | Richard Stuart Harman, Headmaster |
| 2007 | A new Chapel Organ installed |
| 2008 | Third Astro laid on the Middle Playing Fields |
| 2010 | The Uppingham School Sports Centre (USSC) opens (officially opened in March 2011 by Lord (Sebastian) Coe Windmill House acquired to house the RS and Philosophy Department |
| 2011 | Woodfield converted into a Health Centre, and the Sanatorium, previously housed alongside Johnson’s, closes Johnson’s accepts girls from 13+ |
| 2014 | New Science Centre opens (officially opened in November 2014 by Professor Sir Alec Jeffreys) |
| 2016 | Dr Richard J Maloney, Headmaster |
| 2024 | Li Kwok Po House opens as a co-ed day house, in the building previously known as the Thring Centre. Named after Dr the Hon Sir David Li Kwok Po (H 54), the new House takes the total number of houses to 16 |
| 2024 | Uppingham Cairo opens in Egypt |