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@Joseph
It's an old Raleigh - so I guess it's British threaded. The fixed cup (drive / right side) tightens anti-clockwise, which would mean it naturally loosens with forward pedalling, surely? It's quite an annoying issue as it means I constantly have to re-tighten it after a days worth of riding. I was thinking about maybe using Locktite!
What toolkit did you buy? I want to see if there's anything which doesn't have too much extra unnecessary stuff :p Have fun!