He was born in Leamington Spa, Warwickshire. At the time of his birth, his mother was an ex-flying circus wing walker, and his father worked for Alvis Cars in Coventry. He was enrolled in a local private preparatory school in 1969, Arnold Lodge, which he hated attending. He was only marginally less averse to Warwick School, the public school at which he was educated from the age of thirteen. He studied Philosophy and Psychology at the University Of Hull, graduating with a PhD.

Inspired principally by the many books he'd read as a child, Simon Cheshire started writing stories while in his mid-teens. It was only once he'd passed his thirtieth birthday and, as he puts it, "finally accepted that his mental age would never exceed ten, he turned to children's books, and at last found his natural habitat". His first book was published in 1997, and since then his work has appeared in a number of different countries and languages.

His early titles, for Walker Books, were illustrated by the acclaimed cartoonist Hunt Emerson. Among his most successful books have been the Saxby Smart detective stories, widely praised by readers and critics. This is a series of books in which a schoolboy sleuth asks questions of the reader, to create a highly original narrative in which reader and writer interact. There have been eight volumes of Saxby's advantures to date. The first two were published in the USA by Roaring Brook, complete with Americanized text and illustrations by R.W.Alley which show a version of Saxby rather younger than his UK counterpart

Simon Cheshire worked in the book trade until taking up writing full-time in 2001. He was a regular broadcaster on the now defunct national radio station Oneword.

More recently, he has branched out into publishing, re-issuing his own edition of his first three books as "Jeremy Brown: Spy".

Simon Cheshire lives in Warwick, but "spends most of his time in a world of his own".

For 6-9s

• Walker Books 2002; Me And My Big Mouse

For 8-12s

• Walker Books 1997; Jeremy Brown Of The Secret Service
• Walker Books 1998; Jeremy Brown And The Mummy's Curse
• Walker Books 1998; Jeremy Brown On Mars

(These three re-issued in 2004 as a bind-up paperback, Jeremy Brown: Secret Agent, re-issued as a self-published bind-up again in 2010 as Jeremy Brown: Spy; also reissued as iPod apps 2010)

• Walker Books 1999; They Melted His Brain!
• Walker Books 2000; Totally Unsuitable For Children
• Walker Books 2000; Dirty Rotten Tricks (reissued as Bottomby 2010 in a self-published edition)
• Self-published 2010; Pants On Fire

Saxby Smart: Private Detective series

• Piccadilly Press 2007, Roaring Brook (USA) 2009; The Curse of the Ancient Mask and other casefiles
• Piccadilly Press 2008, Roaring Brook (USA) 2010; The Fangs of the Dragon and other casefiles (issued in the USA as "The Treasure Of Dead Man's Lane")
• Piccadilly Press 2008; The Pirate’s Blood and other casefiles
• Piccadilly Press 2008; The Hangman’s Lair and other casefiles
• Piccadilly Press 2009; The Eye Of The Serpent and other casefiles
• Piccadilly Press 2009; Five Seconds To Doomsday and other casefiles
• Piccadilly Press 2009; The Poisoned Arrow and other casefiles
• Piccadilly Press 2010; Secret Of The Skull and other casefiles

• Piccadilly Press 2010; Saxby Smart's Detective Handbook

For 12+

• Piccadilly Press 2003, plus various overseas editions; Kissing Vanessa
• Piccadilly Press 2004, plus various overseas editions; Plastic Fantastic
• Piccadilly Press 2006, plus various overseas editions; The Prince And The Snowgirl

Short stories

• The Giant-Sized Yuck (in Story Of The Year Vol.6, Scholastic 1998)
• The Adventure Of The Dented Computer (in The Young Oxford Book Of Mystery Stories ed.Dennis Hamley, OUP 2003)
• Later (in Like Father, Like Son anthology, ed.Tony Bradman, Kingfisher 2006)

Books for schools

• Hello It's Me (short story in Texting Texting: Science Fiction Stories, Ginn KS2 Guided Reading Programme 2003)
• Tomb Raiders: Discovering Tutankhamun (Treetops True Stories series, OUP 2003; U.S. edition published by Pacific Learning, 2005)
• How To Upset A Victorian (Lightning series for Year 6, Harcourt Education 2003)
• The Scheming Of Morgan Le Fey (in Arthur And The Legends Of Camelot, Lightning Year 6 Plays series, Harcourt Education 2003; reissued in a standalone edition, Pearson Education 2008)
• The Pit And The Pendulum (adaptation of the Poe short story, in All Alone, Navigator guided reading series, Harcourt Education 2004)

Heinemann Primary SEN "Rapid” range, Series 1

• Wild And Windy (Level 4A, Harcourt Education 2006)
• Robots Rule! (Level 4A, Harcourt Education 2006)
• Zoooom! (Level 4A, Harcourt Education 2006)
• Huge And Hungry (Level 4A,, Harcourt Education 2006)
• Double Trouble (Level 4 Benchmark assessment book, Harcourt 2006)
• Fun Or Fear? (Level 5A, Harcourt Education 2006)
• Space School (Level 5A, Harcourt Education 2006)
• Scary Hair (Level 5A, Harcourt Education 2006)
• Fun With Food (Level 5A, Harcourt Education 2006)
• Aliens And Enemies (Level 5 Benchmark assessment book, Harcourt 2006)
• Mystery In The Skies (Level 6A, Harcourt Education 2006)
• Code Breakers (Level 6A, Harcourt Education 2006)
• Dangers Of The Deep (Level 6A, Harcourt Education 2006)
• Ghostly (Level 6A, Harcourt Education 2006)
• Heading For Danger (Level 6 Benchmark assessment book, Harcourt 2006)

Heinemann Primary SEN "Rapid” range, Series 2

• Super-Sized! (Level 3A, Harcourt Education 2007)
• Space Junk! (Level 3A, Harcourt Education 2007)
• Mighty Machines (Level 3A, Harcourt Education 2007)
• Testing Times (Level 3A, Harcourt Education 2007)
• The Last Laugh (Level 3 Benchmark assessment book, Harcourt 2007)

Rising Stars "Superscripts" series, 2007

• Space Raiders
• The Cave Of Death
• Revenge!

• Sam’s Flood Plan (Project X series, Oxford Reading Tree, OUP 2009)