While at Nottingham he sang in the university's opera group chorus and directed a production of Gilbert and Sullivan's Ruddigore at the New Theatre.
[1] His first production for Glyndebourne as the original director was the 1994 Le nozze di Figaro which inaugurated the festival's new opera house and was later released on DVD.
[2] From 1991 to 1997, Medcalf was Director of Productions at English Touring Opera, producing Don Giovanni, The Magic Flute, Orfeo ed Euridice, Rigoletto, Le nozze di Figaro, and L'elisir d'amore for the company.
[1][3] One of Medcalf's earliest productions in Italy was The Magic Flute for the Teatro Regio di Parma in 1995 conducted by John Eliot Gardiner.
He has since returned Guildhall as a guest director, directing Almeida's Spinalba in 2010 and the British and European premiere of Ned Rorem's chamber opera, Our Town in 2012.