[3] Penrose read for her degree at Somerville College at the University of Oxford, where she started as a scholar of Greats (Classics) in 1889; this involved her learning both Latin and ancient Greek from scratch.

[1] At the time, Honour Moderations for Classics were not open to women, so she moved straight to Finals without taking any other examinations during her course of study.

[8] Upon completing her undergraduate studies, Penrose was offered a post by Agnes Maitland, the principal of Somerville, designed to keep her at the college as a combined tutor, librarian and secretary, but instead moved to London.

[9]: 77–78  She taught for a short time as an extension lecturer in Oxford and London before being appointed as Principal of Bedford College in 1893.

[2]: 9 In 1907 Penrose was appointed as Principal of Somerville College, Oxford, following the death of her predecessor, Agnes Maitland.

"[12]: 1  Penrose had also introduced an entrance examination for students seeking to join Somerville in 1908, making it the first women's college to do so.

[1] She had responsibility for a range of war-time roles, including organisation of the National Registration in Oxford, and management of the Belgian Visitors' Committee.

[7]: 140  On her retirement in 1926, she was given a large sum as a farewell present, which she returned to the college to establish a student loan fund.

[1][15] The success of the 1920 campaign to admit women as full members of the University of Oxford owed much to the diplomatic skills and academic reputation of Penrose.

"[7]: 121 Penrose was the subject of numerous photographs[17] and portraits, including by Francis William Helps,[18] Philip de László,[19] and the Rhomaides Brothers.