Coldfusion structures don't have an order, so you can't guarantee when looping over a struct that the keys will come out in the same order they were inserted (or numerically/alphabetically/etc).
If the order is important, use an array instead.
An alternative would be to get all the keys in an array, then order that array, and loop over it, but inside the loop referencing the structure.
<!--- get an array of the keys in the desired order --->
<cfset achievements = StructSort(SESSION.squad.achievements, "numeric", "desc")>
<!--- loop over that array --->
<cfloop index="year" array="#achievements#">
<!--- refer back to the struct, keyed on the current year we're looping on --->
#year# : #SESSION.squad.achievements[year]#
</cfloop>