Brown Sugar Puppy's Sports Challenge was a challenge in Bearville that any user could take part in throughout the entirety of Bearville's life. All users had to do was firstly go to the Skate Park and talk to Brown Sugar Puppy.
He challenges you to beat his best scores in three of the minigames around Bearville; if you beat each score, he would give you a special reward!
- The first game that users had to play was Fast Paw located at the Skate Park. Users had to get at least 15,000 points in the game in order to advance and move onto the next minigame.
- The second game users had to play was Bear-2-Bear Baseball at the Sportsplex; users had to get at least 1,500 points in order to advance.
- The final game that users had to play was Kick-It-Quick; you had to get at least 75,000 points to beat Brown Sugar Puppy's score in this game! Once you had completed this challenge, users had to go back and talk to Brown Sugar Puppy to claim their reward.
The prize users won for completing this challenge was a Sports Challenge Trophy that could be placed anywhere in your Cub Condo. This was available all of the time, though the challenge could only be completed once.