MySQL Query – How to Get Last X Rows Ordered by ASC?

SELECT *
FROM Mytable
ORDER BY
   userID, Date

I assume Date is really a date/time type and not varchar...

Edit, after clarification:

Untested

SELECT
    M.*
FROM
    ( --one row for each user
    SELECT MIN(Date) AS FirstUserDate, userID
    FROM MyTable
    GROUP BY userID
    ) foo
    JOIN
    MyTable M ON foo.userID = M.userID
ORDER BY
    foo.FirstUserDate, M.userID, M.Date;

I would like to get rid of "Using temporary; Using filesort"

One of the problems I see is that you're using different GROUP BY and ORDER BY clauses. From the manual on how MySQL uses temporary tables:

If there is an ORDER BY clause and a different GROUP BY clause, or if the ORDER BY or GROUP BY contains columns from tables other than the first table in the join queue, a temporary table is created.

As soon as you create a temporary table, it will need to be sorted according to your ORDER BY clause, indicated by 'using filesort'.

This execution plan at leasts uses the indexes to appropriately limit the number of rows found.

I would also look through the docs on ORDER BY optimization.