OK, so the reception seemed to be pretty good towards this sort of fun, whimsical challenge. I decided to start with some relatively bigger names in the sport while trying to work through how to map these in the best possible way. Commenter ahoehler helped me through getting these mapped through Google Maps, and through the feedback received in the rest of the comments from the first game, I've landed on how to best make it fair for everyone involved.
When you post your answers, PLEASE USE THE SPOILER TAG. This will help shield the answers from those who want to give it a shot, even if the correct answer has already been given. I have a full-time job and other fun non-TSF responsibilities, but I'll try to keep a close eye out on the comments to make sure the answers aren't purposely being revealed in the comments, and if there's a comment that's been posted without the spoiler tag I'll delete it so it doesn't ruin it for others.
Harold Harpoon provided the correct answers to all four the first go-around, which means he's in the lead with four points going into this week.
Remember, the order of the maps goes:
1. Current Arsenal player
2. Current Euro-based player
3. Current Euro-based player
4. Retired player
You'll quickly notice with these maps there are no country borders or labels, so it takes both geographical acumen in addition to knowing who played where to get the answers. Additionally, the pinpoints aren't labeled, so you have to find the start of the path yourself. Good luck, remember that the maps contain loan destinations, and to add spoiler tags to your guesses.