Sports can be expensive. Ice time for hockey practice to $200 tennis racquets can discourage some participants. From billion-dollar teams and venues to Olympic Games costing billions as well, where will sports get all the money they need to operate? One vehicle that has been used successfully for almost 100 years has been postage stamps. Funds were not generated just from selling Olympic themed stamps that generated some money for the postal service or maybe a government. The bulk of funds associated with sport-related stamps fundraising has been through semipostal stamps. Semipostal stamps provide for an additional charge over the face value with those funds going to a worthy cause. Worth causes over the years have included tuberculosis research/treatment, disease prevention, supporting the Red Cross, feeding the poor, or winter heating aid. Another beneficiary has been sports. Researching Scott Stamp Catalogues from the 1920s through 2015 has highlighted 60 countries who have issued 920 semipostal stamps to fund everything from Olympics to youth sports, sport venues, and even sport equipment purchases. This article examines how these stamps have been used successfully in the past and how they are still being used. Furthermore, one country, Germany, has been issuing sport-related semipostal stamps for over 50 years and has generated millions of dollars and sold over 250 million sport-related semipostal stamps.