The brief review in Melody Maker discussed the origins of the album's title and added simply, "It sounds poetic and so does composer, singer and guitarist Nick Drake.

"[10] In October 1969 Gordon Coxhill of the NME expressed his disappointment with the record, saying, "I'm sorry I can't be more enthusiastic because he obviously has a not inconsiderable amount of talent, but there is not nearly enough variety on this debut LP to make it entertaining.

"[11] A review the same month by Maurice Rosenbaum in The Daily Telegraph was more positive, describing the record as an "excellent LP of [Drake's] own songs", and observing, "His voice is slow, reflective and warm, and although the verse structure tends to melodic monotony, there is no mistaking the quality and the promise of 'River Man', 'The Thoughts of Mary Jane', 'Man in a Shed' and other items on this disc".

A 1989 retrospective assessment of Five Leaves Left by Len Brown in NME awarded the album 9/10 and stated that it "remains a masterpiece of English melancholy; a moving work that first revealed Drake's remarkable talent to communicate his fears of passing light and life, with simple beauty; his skill to charge listeners with emotions equal to his own".

[16] Including it in a 1999 list of twelve of "the best folk albums of all time", Q in 1999 called it "the pinnacle of a melancholy canon of work so distinctive that admirers can only speculate miserably on what might have been".

[22] A 2007 review by Chris Jones for the BBC said, "it's hard not to be still floored by the beauty of [Drake's] first album" and lauded its "unique vision" mixing elements of English folk music and jazz.

John Harris wrote in Q that "the record's abiding impression" was of "a hesitant, slightly troubled soul peering at the straight world and wondering what will become of both him and the people he beholds".