Two phrases "won medal up" and "won medal down" is from the song "Come out ye black and tans" and I truly can't understand it 🙁
"Come out you black and tans,
Come out and fight me like a man,
Show your wife how you won MEDALS DOWN in Flanders;
Tell her how the IRA made you run like hell away,
From the green and lovely lanes of Killeshandra. "
"Oh! Come out you British Huns,
Come out and fight without your guns,
Show your wife how you won MEDALS UP in Derry;
You murdered sixteen men and you'll do the same again,
So get out of here and take your bloody army".
Best Answer
Searching for the lyrics, I found this line
at
lyrics.com song
The phrase means simply "toward the south in Flanders".
I didn't find "won medals up", although it might appear in another version of the lyrics.
Added 11/28 You've added lyrics that contain "...won medals up in Derry..."; that usage is analogous to "down in Flanders", so it probably means "to the North in Derry".