Underdog Analytica was born out of the frustration and contempt many sports bettors have for the lack of transparency and integrity in the handicapping (selling match predictions) industry. Dishonesty was accompanied by emotional bets with no statistical backbone, and innovation was crucial. We utilize a machine learning algorithm to build a portfolio of statistically-backed match predictions that our users invest in. Our strategy depends on applying the same financial risk to ~20 positive-odds bets. Currently, we offer our predictions to users for free as we build the backend of our enterprise. We plan to charge users a subscription cost for our portfolio on a monthly basis, then establish a fund for hands-off investing. Underdog Analytica views sports betting with an extended time horizon instead of the typical get-rich-quick schemes found elsewhere online because our investment strategy depends on statistics and data analytics. We acknowledge the presence of negative and positive weeks but believe that high volume betting on this method produces returns. The 2020-2021 season proves it!