Recently I took the Glossop line off because of issues with the route etc. I read after the latest update it has been fixed, went on Steam but when I clicked on it it isn't showing in my library does this mean I have buy it again or am I missing something? Col.
You click it in your list of DLC - Right click game, Properties, DLC tab, search or scroll, tick in. Are you signed in to Steam where you're looking at it? Browser cookies are really short and require 2FA pretty much always, even from the same PC where Steam is running. You could also check your Steam purchase history to verify that you obtained it. It may have been refunded or subject of a chargeback. You should remember but anyway.
You have also posted this in the TSC section! Glossop is a TSW add on (TSC gives us the complete Woodhead Line). However the answer is still the same, just retick the DLC.