Tic-Tac-Tough is an online JumpStart game that was first released circa 2000. It's a basic tic-tac-toe game with a sports theme. The player's opponent is Casey Cat, although he doesn't have any visual appearance here, there are only voice clips for him. The game has three possible outcomes, either you win, Casey wins, or you tie. This video covers all three outcomes.
This and similar JumpStart web games are all .dcr files, which are kind of difficult to get working with modern operating systems and browsers. I also have a feeling these games might be taken down at some point (as of now, they're still accessible from reg.knowledgeadventure.com), so I wanted to record some footage in case that happened.
Disclaimer: I own nothing in this video, all rights are reserved by the respective owners.