Also- I was reading that class (PrintWriter) documention and from my understanding it will always truncate the file. Also it will create the file if it does not exists (ie you can comment out your new File statement since you are not doing anything special with the File object before passing it to the printwriter)
Edit:
What I mean is that you will always be overwriting it so if you only write one player/score then there would only be 1 entry- so I would suggest in memory collection as Fou-Lu stated. But I could have misread that Class document as well