The school was created by merging two Evesham schools - Simon de Montfort Middle School and Evesham High School, in 2014, when the Middle School had been taken into special measures..They had previously been run in a "hard federation", and already shared staff and the board of governors. These proposals were approved by Worcestershire County Council after a consultating with staff, parents, students, and the Secretary of State for Education on. The previous schools, Simon de Montfort Middle School and Evesham High School had received "Good" ratings from Ofsted in March 2014 and September 2011 inspections. Evesham High School Sixth Form previously received a "Satisfactory" rating in its September 2011 Ofsted inspection report with the report specifying a "good capacity to improve". After the merger, however, GCSE results for the De Montfort School in the 2015 academic year fell well below the government standard for attainment with just 32% of students achieving the baseline 5 GCSEs at C-grade and above. The Department for Education ranks the school in the lowest 10% of schools in England at the primary level and lowest 30% at the secondary level, describing it as "well below national average". As of September 2019, The latest DfE performance tables show The De Montfort School in Evesham now sits within the top six schools out of 30 Worcestershire high schools. The school is now well within the ‘above average’ category of all schools and is the most improved school in Worcestershire and predicted to fall within the 5% of most improved schools. It also received a positive Progress 8.
Worcestershire operates a three tier system of first, middle and high schools. The De Montfort School is an all-through school where most pupils enter the middle school at the age of ten, and have an automatic transfer to the high school at thirteen. The admissions procedure is handled by Worcestershire County Council. The school has 3 entry points at year 6, year 9 and year 12. Entries at year 6 are predominantly from its feeder schools St. Richard's C of E First School and Bengeworth Academy, but entries from other local schools are sometimes made. Entries at year 9 are predominantly made by students who studied at the school during year 8, but a significant number are also made by students from Blackminster Middle School. Entries at year 12 normally come from the school and varied set of institutions and from other local secondary schools.