The first game in the history of the Century League took place on April 22, 1876 with Boston visiting Philadelphia. The visiting squad won the game by a score of 5-2 with Boston's Ted Maston getting the first hit in league history and Daniel Fallow notching the victory. In honor of the Centennial Exhibition that would take place in Philadelphia that summer, the Philadelphia squad became known as the Centennials while Boston was dubbed the Pilgrims. 

The other clubs to take the field in that inaugural season included the Brooklyn Unions, St. Louis Brewers, Chicago Chiefs, Cincinnati Monarchs, New York Knights and Detroit Woodwards. Though the new endeavor qualified as a success, there was a major bump in the road at the end of the first season. Both the New York and Philadelphia clubs, citing financial reasons, elected to not make their final road trips. This caused issues with the championship for the first season - Philadelphia won at the highest percentage of all teams (71.7%) but had only 43 wins because they failed to make their final trip to the west. Boston, playing more games than anyone else, won 47, the best total in the league, but also lost 23. Brooklyn won just one fewer than Boston but lost three fewer games (46-20). So which club was the champion? 

William Whitney's own club had finished fourth with a 39-26 record and as league president, the argument ultimately came to his desk. Controversially, he awarded the title to Boston by virtue of their 47 victories. Brooklyn's Miles Bigsby's vigorously protested this. Philadelphia's Jefferson Edgerton wisely accepted the decision - he was on thin ice already. The biggest protests came from teams not involved in the championship dispute: Cincinnati and St. Louis who were deprived of revenue due to the cancelled games they were supposed to play in hosting New York and Philadelphia.

St. Louis finished fifth (28-36), followed by Detroit (23-46) and Cincinnati (20-49). New York had the best case for quitting early - they were in last place with a dismal 14-43 record.

Philadelphia's Roy Frazer won the first batting title in league history with a .379 mark. Boston's Arthur Friermood (.369) and Cincinnati's Paddy O'Hanlon (.367) were close behind. Brooklyn's Hartigan O'Carroll had the league's best ERA (1.46) while Boston's Daniel Fallow led the circuit in victories (28). 

The first season had proved that the concept of a professional baseball league could work, but it wasn't all good news. The league was not yet a full calendar year old and William Whitney had his first crisis. When he refused to acquiesce to the demands of St. Louis and Cincinnati to expel the New York and Philadelphia clubs for failing to adhere to the league's schedule, Whitney saw the Monarchs and Brewers leave after just one season. In the long run, the decision to keep the nation's two largest cities in the league would prove correct; at the time however, it seemed like a mistake.