Here is a list of how to get the medals:
1.Grade cup:Cup C,D,B,A,S-win in all
2.Version cup:VER1,2,3,4,0-win in all
3.Type cup:Fire,Grapple,Thunder,Wind,Nature,Cool,Metallic,Filth-win in all
4.Special cup: Dino, Wing,Animal,Human-win in all
5.100 times win: win 100 championchips in the area.
6.Technique Master: Mastered all techniques.
7.Digimon Master: Raised all digimon[on chart]
8.Max abilities: maxed all of your digimons parameters.
9.Perfect curling:Get a perfect score in curling.
10.100 fish: caught 100 fish.
11.Ending:finished the game[Defeted Analogman once]
12.Town Flourishing: Recruit all digimon
13.Card complete:got all Digimon cards[to get the last card defeat the 1st Machinedramon]
14.Bits maxed:Colleced 999,999 bits.
15.10 years:Survived 300 days