The athletic association played its home games at CAA Field (formerly South Side Park),[1] located on the corner of 35th Street and Wentworth Avenue in Chicago.

[22] Duquesne Country and Athletic Club (DC&AC) would also release their schedule for the 1895 football season, which included a game with Chicago AA on November 9.

[25][26] October 22: Mr. Mulliken, a man with past experience at Columbia and on the Crescent Athletic Club of Brooklyn, decides to join the Chicago AA eleven.

[27] The contest was yet another blowout for the semi-professionals, as Rush-Lake Forest suffered from injury, and CAA's FB Brown had a perfect 5 for 5 PAT streak, culminating in a 30 to 0 shellacking of the makeshift college team.

He asserted that "if yesterday's showing is a test of the ability at the game, it [The Chicago AA team] would have to work hard to defeat the Yohokas Pigskin Pelters or any like organization."

With 10 seconds remaining, it was still Chicago's possession, and with one last shove at the Newton defensive line, fullback Brown rolled into the endzone over a mass of players, achieving a walk-off touchdown and subsequent PAT.

Stevenson was the center of attention for the Athletics, holding the line firm and knocking back Newton's star player, Mr. Draper, numerous times throughout the contest.

Penn was furious after the game, and on November 7, they officially declared that the school would never play another athletic club, association, or non-collegiate team again, cancelling their 1895 matchup against undefeated Boston AA.

[44] November 5: The CAA was again dubbed champions of the West, this time by The Sun (New York City), ahead of their match against the Orange Athletic Club.

Although this was a crushing defeat, CAA did not lose its contention for Champions of the West, as Eastern organizations like Orange AC did not hold much weight in the "standings" that sportswriters in the Midwest factored into their opinions.

There was betting among the spectators that Chicago AA would reach the "century-mark" (100 points), which at that time was incredibly more common than it is in the modern (post-WWII) era of football.

For the first time in 1895, two different men scored PATs for the Athletics, Huddelson with three and Brown with one, and CAA also got its first known points off of the other team, when they blocked a kick in the endzone and DC&AC player Vaill fell on it for a safety.

Stevenson, Barter, Hadden, and Blaney did not leave with the team though, instead staying in Pitt to hear cash offers from the Duquesne and Pittsburgh Athletic Clubs to play for them instead.

[55][56][57] November 13- Bob Wrenn, Harvard's star quarterback, agreed to play his position for CAA in their Thanksgiving Day game against Boston AA.

[58] November 14-The football committee of the Chicago Athletic Association held a meeting on their current roster, and decided it would not be good enough for their games ahead.

Manager Cornish was told to scour the Northwest for players, and to especially seek out the infamous "Pudge" Heffelfinger, who was currently coaching at Minnesota, along with any good halfbacks and tackles.

[60] November 20- The infamous Pudge Heffelfinger becomes the first man to accept manager Cornish's call for players, and agrees to play with the CAA in their Thanksgiving Day contest.

Thomas scored the single CAA touchdown in the 2nd half for a bare 4–0 win, defeating any chance for the ILA to avenge their late October loss.

[67] November 26- In an article for the Daily Inter Ocean, Pudge Heffelfinger declared that this Thanksgiving contest would be his last appearance as a player or coach, and he is retiring from athletics to get married.

The Chicago AA colors of cherry, black, and white, were seen on streamers, banners, pins, ribbons, and commemorative buttons were worn and sold throughout the day.

The matchup of tackles Pudge Heffelfinger for CAA and Bert Waters for BAA was highly coveted, as both men had been All-Americans multiple times, and were heralded as "the heroes of many hard-fought games, and each will try to outplay the other."

Including both teams, members of former colleges had come from Harvard, Yale, Knox, Dartmouth, Wisconsin, Northwestern, Boston University, MIT, Minnesota, Michigan, and Butler, some very recently, to play in the athletic club's season, or just for the Thanksgiving Day game.

Richards, a recent addition to the Chicago AA lineup, made his first yards for the CAA, running through BAA right guard LeMoyne for another short gain.

The game tempo began to speed up, with both teams beginning to play fast, continuing their tactics of attacking the weak side of the line for small gains.

Boston AA kicked for the third time in a row (most likely attempting to run out the clock, as that was seem as a legitimate option in 19th century football), and Richards plunged into the snow on the sideline and fell on it.

It looked like CAA would tie the game up with three short gains by Heffelfinger, but a fumble on a backwards pass lost this advantage, and Boston AA recovered.

With the ball in the hands of Jesse Van Doozer, the Chicago AA sat back, and watched the Nebraska native wrap up 6 gains on downs, greatly helping to achieve their first, and only touchdown of the day.

The CAA crowd cheered with excitement, thinking they were about to win the brutal Thanksgiving Day contest, but Brown missed what was called a "sure goal", the score stood, tied 4 to 4.

Many praised Van Doozer, Heffelfinger, Stevenson, Bert Waters, and Curtis for their excellent play, and the game was deemed very clean, with the sole blemish being the scuffle in the 1st half.

Those players were Fred Slater, Paul Brown, Ben Thomas, CB Coffeen, DA Stone, Harry G. Hadden, Archibald Stevenson, JR Huddelson, Aldrich, and Olin McCormick.