There are two reading orders: the original one when the books were first published, and one the series acquired in the 1970s when Knight produced its first full run of the paperbacks.
The original publication and reading order of the Jill books is:
1 – Jill’s Gymkhana (1949)
2 – A Stable for Jill (1951)
3 – Jill Has Two Ponies (1952)
4 – Jill Enjoys Her Ponies (1954)
5 – Jill’s Riding Club (1956)
6 – Rosettes for Jill (1957)
7 – Jill and the Perfect Pony (1959)
8 – Pony Jobs for Jill (1960)
9 – Jill’s Pony Trek (1962)
Knight changed the reading order of the entire series with their 1970s printing of the paperbacks to:
1 – Jill’s Gymkhana
2 – A Stable for Jill
3 – Jill Has Two Ponies
4 – Jill Enjoys Her Ponies/Jill and the Runaway
5 – Jill’s Riding Club
6 – Challenges/Pony Jobs for Jill
7 – Jill and the Perfect Pony
8 – Rosettes for Jill
9 – Jill’s Pony Trek
Rosettes and Pony Jobs/Challenges change places. Why Pony Jobs should be read at number six is a mystery: it is very obviously the last chronologically, with Jill and Ann both having left school.
The first pictures below show the reading order as printed on the original hardbacks. The numbering was introduced from Jill Enjoys Her Ponies (number 4) onwards. Later reprints are often numbered – I have a later hardback printing of Stable which is numbered.


The 1960s Knight paperbacks with Bonar Dunlop covers are numbered to some extent. My edition of Jill’s Gymkhana isn’t numbered, but it might well be reprints were. I don’t have all the titles in this edition, but here are the ones I do have.

The 1970s Knight paperbacks with W D Underwood covers are all numbered, and here they are:

The series kept the new numbering up to the 1990s black horseshoe edition (if you’re keen eyed you’ll notice I don’t have a full set of those). No full sets were printed after that point until the JBB reprints, which returned to the original reading order.

