Should listed citations in a historical overview be ordered numerically or chronologically?
If you adopt an official citation style, then this will dictate the rules for ordering in-text citations and end of document references.

In-text citation ordering rules

When  multiple authors appear in one citation block, then there are various rules depending on the citation style: (a) alphabetically by first author surname, (b) arbitrary when using a numbered reference style, except are typically consecutive (e.g., 1-3, or 1,3,4), although based on @Jessica's answer ordering may not be required by all style guides.

End of document reference ordering rules

Two common rules are (a) alphabetically by surname and then by year for papers by the same author (e.g., APA style), (b) in order of appearance in the manuscript (i.e., when using superscript numbers).

General points about showing historical development of ideas

If you want to show the development of ideas include something in the text that indicates this development.  For example ,


  Jones (2000) was the first to propose the idea. Several researchers further developed the idea including Smith (2005),  Brown (2007), and then Cooper (2009).


or euivalently:


  Jones (1) was the first to propose the idea. Several researchers further developed the idea including Smith (2),  Brown (3), and then Cooper (4).