Both this achievement and
are glitched in your favor. This is because, when playing a level, if you finish the level with a silver medal for deaths, time, or both, it will count for these achievements once. Then, if you get a gold medal during a later run of that same level, the golds will count again for the silver medal tracker, giving you up to 4 silver medals per level for the tracker as opposed to the intended 2. This only works if you get a silver before the gold for a level, because getting a gold initially will only count for the one silver medal as opposed to the possible two. Using this method, you can get this achievement as early as the first winter level.