The Owls inaugural season in PFLA was not a successful one: they finished last in the league's Eastern Division with a 3–9 mark. Nor did they play in Chicago; the Owls' home games were in suburban Niles, Illinois, at Notre Dame College Prep School, where they played in front of a few thousand fans per contest. (Future baseball star Greg Luzinski attended and played football for Notre Dame at the time.) Bob Webb, who grew up in nearby Gary, Indiana, was the Owls' main quarterback; he would remain with the team in 1968.
After dropping four of their first five games, the Owls fired Branby and replaced him with Webb, who was still the Owls' backup quarterback. Webb led Chicago to a 5–2 record the rest of the year, enough to even up the Owls' record at 6–6, third place in the Central Division. Playing primarily on Saturdays, the club drew only 35,835 fans to cavernous Soldier Field all season, or less than 6,000 a game.
1969 season
Things did not improve for the Owls in 1969, as their record slipped to 5–7 and continued to draw small crowds: just 21,403 paid their way to their games this season, barely 3,500 a contest and a small fraction of their stadium's capacity. The team was practically invisible amid the crowded Windy City sports scene, with a running gag in the Chicago press that mentions of the Chicago Owls brought a response similar to an owl's hoot: "Who?"[3] The CoFL revoked their franchise on December 15, 1969, for failing to meet the league's financial obligation[4] (this would soon become moot, as the entire CoFL would fold soon after). Despite this setback, the Trans-American Football League announced it would include the Chicago Owls on its schedule for 1970,[5] but the team folded prior to the start of the season.