For many of us, this achievement should come naturally when going for the Joe Montana Award
You have to create your own QB within Connected Careers, Online or Offline, then over the course of 4 seasons (the minimum needed for this achievement) you have to progress through the regular season (pre-season doesn't count) then win every game in your post season. You will know when you have won the superbowl as you gain 10k XP for it.
If at any point you wish to check how many superbowl wins your QB has, you can check one of 2 ways. Firstly go to the My Career tab, press LB or RB twice then Look under Superbowl wins, Or you can Check by Checking your Legacy Score and it should say under your character how many Superbowl wins you have.
As far as I am aware, there is no difficulty limitations so if you struggle drop your difficulty to Rookie. I also presume you can save and simulate the game so you don't have to play and if you win you advance, if not re-load.
Also Depending on whether you are going for a 99 Overall Player with your QB you will also probably gain this achievement when working on the following achievements.
The Peak Performance achievement in Madden NFL 13 worth 364 pointsAs a created player, achieve a player rating of 99 overall in Connected Careers. The Overall 90 achievement in Madden NFL 13 worth 70 pointsAs a created player, achieve a player rating of 90 overall in Connected Careers. The 85 Overall achievement in Madden NFL 13 worth 33 pointsAs a created player, achieve a player rating of 85 overall in Connected Careers. The 80 Overall achievement in Madden NFL 13 worth 14 pointsAs a created player, achieve a player rating of 80 overall in Connected Careers. As well as these related achievements:
The Hall Of Famer achievement in Madden NFL 13 worth 447 pointsAs a created player or coach, get inducted into the Hall of Fame in Connected Careers.