Starlin Castro is the only Cub player to have a sticker in each of the five sets, so I'll use his stickers to look at the run.
Retired players started showing up in the Cubs sets in 2013. Being the creative folks that they are, Topps has given us...
Let's end with a view of all five year's worth of stickers. It's a bit small, but you can see all of a season's stickers in one row.
Here's a little better look,
with each year getting two rows instead of one.