Bertrand skrev den [[2. februar]] [[2015]] under på en permanent 4½-årig aftale med Southampton for en ukendt transfersum,<ref>{{cite web|title=Bertrand joins Saints on permanent deal|url=http://www.saintsfc.co.uk/news/article/20150202-ryan-bertrand-permanent-southampton-chelsea-deadline-day-2244851.aspx|publisher=Southampton FC|access-date=8. november 2015|date=2. februar 2015|archive-date= 3. februar 2015|archive-url=https://web.archive.org/web/20150203011412/http://www.saintsfc.co.uk/news/article/20150202-ryan-bertrand-permanent-southampton-chelsea-deadline-day-2244851.aspx|url-status=dead}}</ref> estimeret til £10 millioner.<ref>{{cite news |last1=Mackay|first1=Hamish|last2=Harris|first2=Nick|title=Ryan Bertrand joins Southampton for £10m from Chelsea on four-and-a-half year deal |url=http://www.dailymail.co.uk/sport/football/article-2937145/Southampton-sign-Ryan-Bertrand-10m-Chelsea-four-half-year-deal.html|access-date=8. november 2015 |work=Daily Mail|date=2. februar 2015}}</ref> Den 26. april blev han som den eneste spiller for Southampton udvalgt som en del af [[PFA Team of the Year]].<ref name=six>{{cite news|title=PFA Team of the Year: Chelsea have six players selected|url=http://www.bbc.co.uk/sport/0/football/32472834|access-date=8. november 2015 |work=BBC Sport|date=26 .april 2015}}</ref>
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