Not being a big sports fan, I found WinTheTrophy to be interesting in a different way: I wanted to see if there was a simple set of rules one can follow to consistently win more than what was bet. After a week or two of trying different strategies, I realized the following observations:

• On average, no one knows the future. That is, if you were to randomly bet on all the teams, your winning percentage will be close to 50%.
• If the above point is true, you should bet more on the team in a given game with the largest payout.
• However, you must make sure you gain the advantage of statistical significance: bet on as many teams as possible in a given day.
• As you win, continue betting on other teams the next day to take advantage of "compounding interest": the more chips you gain, the more you can bet on the following day (until your chip count is reset the following week).
• This strategy has a weakness of being very naive: you might not want to bet against a team with a perfect winning record playing a team with a "perfect" losing record, for example. However, even with this weakness, this strategy has on average won twice the amount that I bet for a given week. 

After seven weeks of betting, I stopped because I became bored with the copious amount of clicking required to play using my particular strategy (i.e., as many bets as possible on high-payout picks). (Again, I’m not a big sports fan.) However, if (when?) WinTheTrophy offers rule-based betting (or bots, as they’re usually known), I plan on taking advantage of them.