Raglan was born in Wythenshawe, England, but grew up in Tenerife, and spent his youth associated with UD Guargacho, Juan Miguel, and CD Marino. He returned to England and came through the Port Vale youth academy to sign professional forms with the club in June 2011, having just been voted Youth Player of the Year. He spent October 2011 on loan at Conference North club Hinckley United; the deal was later extended to cover the month of November. He scored for Hinckley in a 3–3 draw at Blyth Spartans. He helped the "Knitters" to the First Round of the FA Cup, after playing in all five qualifying matches. He then gave away a penalty against Tamworth in a 2–2 draw at De Montfort Park, before a 90th-minute strike from Kieron St Aimie won the tie for Tamworth at The Lamb Ground. He returned to Vale Park in December, having played fourteen games for Hinckley, half of which were in the FA Cup. He joined Hinckley on a permanent basis in the summer after Vale manager Micky Adams 'reluctantly' opted not to offer him a new contract at the club.
Raglan signed with Chesterfield in April 2014, with manager Paul Cook describing him as "very much one for the future". He made his League One debut on 30 August, coming on for Sam Hird 29 minutes into a 2–1 victory over former club Port Vale at Vale Park. He marked another milestone against his former club, scoring his first Football League goal in a 3–0 win over Port Vale in the return fixture at the Proact Stadium on 10 January. He made a total of 25 appearances in the 2014–15 season and helped the "Spireites" to the play-offs, where they were beaten by Preston North End at the semi-final stage. He signed a new contract extension at the start of the 2015–16 season, keeping him tied to the club until summer 2017. He underwent hernia surgery in February 2016.
Oxford United
He joined Oxford United on a five-month loan deal on 31 August 2016. Manager Michael Appleton said that "we were looking for someone to cover us at centre-half with Curtis Nelson, Aaron Martin and Joe Skarz all struggling right now and he fits the bill perfectly." In January he extended his loan deal until the end of the season despite being kept out of the first team by the form of Chey Dunkley and Curtis Nelson. He played a total of 16 games for the "U's" during the 2016–17 campaign, before being released by Chesterfield in May 2017. He signed a two-year contract with Oxford the following month after stating that "I thoroughly enjoyed last season". He ruptured two ligaments on the eve of the new season and was ruled out of action for three months. His injury left him unable to feature under manager Pep Clotet, and with the arrival of Robert Dickie caretaker-manager Derek Fazackerley felt that he had enough cover at centre-back to allow Raglan to look for game time elsewhere. On 30 January 2018, he re-joined former club Port Vale in League Two on loan until the end of the 2017–18 season; manager Neil Aspin had quickly needed a centre-back to replace the recalled loanee Tom Anderson. He made an excellent debut by helping the "Valiants" to keep a clean sheet in a 0–0 draw with Morecambe at Vale Park on 4 February. However he was dropped after a poor performance in a 5–1 defeat to Cheltenham Town six days later, before making a good impression upon his return to the team four weeks later in place of the injured Kyle Howkins.
Cheltenham Town
On 15 January 2019, he joined League Two side Cheltenham Town on loan until the end of the 2018–19 season, having played against the "Robins" earlier in the season in the EFL Trophy. Oxford Head CoachKarl Robinson said that "we can't offer him that on a regular basis right now we have Curtis Nelson and Rob Dickie playing regularly plus John Mousinho and Sam Long". He went on to make 19 appearances for Cheltenham, being utilised on the right of a back three alongside Ben Tozer and Will Boyle by manager Michael Duff, helping the club to a 16th-place finish. He was released by Oxford on 9 May and signed a two-year deal with Cheltenham five days later. He had a strong 2019–20 season and was named in five out of eleven journalists 'League Two team of the season ' after the COVID-19 pandemic in England caused the season to be put on hiatus on 15 March. The season was ended early with Cheltenham in the play-offs and Raglan scored the opening goal of the semi-finals, a 2–0 first leg victory at Northampton Town on 18 June. However Cheltenham went on to lose the second leg at Whaddon Road by three goals to nil and were eliminated from the play-offs.
