Uptown Sports was founded in 1983, by Donald G. Reynolds. Don has served as the President of the company since its inception, and has been involved with thousands of players over the past twenty five years.

Reynolds founded the company while leading an extremely successful career in the insurance industry. One of the most successful men in the Canadian insurance business, Reynolds extended his hand into the hockey world after being approached by members of the Toronto Maple Leafs, who were clients in his insurance practice.

As Reynolds garnered a reputation as an honest and hard working advocate for his clients, Uptown Sports continued to grow, both in terms of NHL clientele and success. The culmination of Reynolds' early efforts in the hockey business was at the 1990 NHL draft, when Uptown client Keith Primeau was selected 3rd overall by the Detroit Red Wings.

As Uptown Sports continued to achieve success in the hockey business, its base of employees grew when Todd Reynolds, fresh off of a professional hockey career of his own, joined the company in 1997. In a very short period of time Todd was able to develop a reputation as a first class individual amongst people in hockey, and his efforts led him to represent some of the best young talent in North America including Carlo Colaiacovo, Mike Fisher, Chris Neil, and many others.

Through the hard work of both Don and Todd, and their commitment to integrity and representing players 'the right way', Uptown Sports continued to be a source of integrity and honesty, in an industry where qualities of that sort are not overly common.