The Windy City’s Open Cup Derbies go Way, Way Back

Ahead of an all-Chicago clash in the 2023 Open Cup between the House and the Fire, we take a look back at the city’s most iconic derbies from the first 25 years of American soccer’s oldest tournament.
By: Charles Cuttone

The upcoming matchup between amateurs Chicago House AC and the Chicago Fire of MLS has stirred up a lot of interest, being a rare intra-city matchup between a pro and amateur team in the Open Cup.

But Windy City derbies are deeply rooted in the history of the competition, dating back to a pair of them (played on the same day) in the very first edition of 1914.

Here’s a look at some of the most iconic Chicago derby games through the tournament’s early history.

1914 National Challenge Cup/Open Cup

December 7, 1913 | Second Round
Pullman 3 - 0 Campbell Rovers

Even as defending champions of the Chicago Soccer League, Chicago Pullman FC had something to prove in their first match of the National Challenge Cup (as the Open Cup was then known) against the Campbell Rovers, having lost to the Scottish club in their most recent league contest 2-1.

A typical Chicago winter day left the field at Fifty-Second Avenue and Madison frozen solid. The wind whipping in off Lake Michigan made the conditions even harsher, but the railroad car makers were quick to take advantage.

McNaughton and Mackie scored first-half goals, and Pullman's defense didn’t allow a shot to get through to their goalkeeper Sutton, who only handled the ball twice in the first half -- both times on goal kicks.

The Rovers came close to scoring early in the first half, when Williamson’s shot went past Sutton, but right-back Ben Govier managed to clear the ball off the line to preserve the clean sheet.

Before 15 minutes had passed in the second half, the Pullmans sealed their ticket to the next round when Albert Shallcross pounced on a mis-cleared ball and put it into the net.

Hyde Park Blues 2 – 0 McDuffs

The Windy City weather was also in play at the day’s other Challenge Cup derby, held at Aviation Field at Sixteenth Street and Forty-Eighth Avenue. Cole, who was not expected to be with the team, gave the Blues the lead and Mair carved out the final margin.

In the days before substitutions were allowed, each club finished the game shorthanded as McDuffs' Hallsall and the Blues’ Jack Evans left the field late in the game owing to the frigid conditions.

March 8, 1914 | Third Round
Pullman 4 - 2 Hyde Park

The third Derby of the first Challenge Cup ensured that one of the city’s representatives would make the Last Eight of the tournament. Once again weather was a factor in the Third Round derby, but where December had been frigid and windy, the March match was played on a field made muddy and heavy by the process of removing snow.

The first attempt to play the game was postponed and a makeup date was imposed when the clubs could not agree -- and referee Walter Napier deemed the field playable despite the poor conditions.

The Carmakers took a 3-1 first-half lead, ultimately closing out the game with two goals from Pollitt and single tallies from Albert Shalcross and Mackie, while the Blues' two goals both came from Wright.

Despite dominating both the Windy City derbies, Pullman’s Challenge Cup journey came to an end in the next round, as they made the trip to Niagara Falls and fell to the Rangers 2-1.

1915 National Challenge Cup/Open Cup

October 18, 1914 | Qualifying Round
Bricklayers and Masons FC 6 - 2 Calumet

With the growth of interest in the Challenge Cup after the inaugural edition, and 82 teams entering the competition, a qualifying round opened the way for another slew of Chicago derbies and a debut for the storied Bricklayers.

The Bricklayers, who would eventually become only the second Chicago team to reach the Cup final, had no problem in the maiden game of the competition, easily downing Calumet 6-2 behind braces from Galbraith and Whiteside.

November 15, 1914 | First Round
Bricklayers 5 - 3 Hyde Park Blues

The Brickies continued their goalscoring barrage against local opposition, moving into the Second Round with a 5-3 win over the Hyde Park Blues on a wet pitch at Fifty-Second and Cottage Grove. Taking a 2-1 lead into halftime, Galbraith recorded his second straight two-goal game for the Bricklayers while Weston also had a pair and Whiteside added one more.

Marley did all the heavy lifting for the Blues, scoring all three of their goals.  

McDuffs 5 - 1 Campbell Rovers
The other first-round Chicago Derby, contested at Forty-Eighth Avenue and Sixteenth Street, was also a goal-fest, especially in the second half. The McDuffs led 1-0 at the interval, then poured it on in the second half with the wind at their backs, scoring four times.

Monroe led the way for the Scots with a hat trick.

DECEMBER 13, 1914 | Second Round
Pullman 1 - 0 Bricklayers

Even with the expanded number of teams and a play-in stage added, Chicago Pullman didn’t get a derby until the Second Round, advancing out of the First Round with a 3-0 win over Roses FC of Detroit, setting up a showdown with the Bricklayers.

Perhaps befitting the contest between the two best teams in the Windy City, this derby was played at the White Sox Park, the concrete-and-steel baseball stadium built just a few years earlier by Charles Comiskey and which later came to bear his name.

The single-deck covered grandstand didn’t do much to protect the players from the windy conditions. Playing into the wind in the first half, the Pullman’s couldn’t solve the puzzles presented by either Bricklayers goalkeeper Harry Birchall or the snow-covered pitch. But 15 minutes after the switch of sides, Albert Shallcross found the net, and the Carbuilders closed out the game despite finishing a man down when McNaughton was sent off.


Pullman got past Packard FC of Detroit in the Third Round (1-0) but their Cup hopes were dashed by Homestead Steel FC (of Pennsylvania) 2-1 in the Fourth Round.

1925 National Challenge Cup/Open Cup

MARCH 15, 1925 | Western Semifinal (Second Replay)
Canadian Club 1 - 0 Harvey

Chicago Cubs legend Ernie Banks was famous for saying "let’s play two." But how about let’s play three? That’s exactly how many times Canadian Club had to face off against Harvey in a Chicagoland derby en route to becoming the city’s first National Challenge Cup/Open Cup Finalist.

Both teams had to navigate a pair of derbies in order to get to the Third Round. Harvey dispatched North Shore 3-0 and Olympia 2-0, while Canadian Club had to get past in-state rivals Gillespie 3-0 before knocking off the Pullmans (2-1).

In their first meeting, on March 1 at Sparta Field, the teams played for two hours to a 1-1 draw, Paxton scoring for the Canadians and Bennett for Harvey.

Back at 27th Street and Kostner Avenue a week later, it was another two-hour battle ending with the clubs knotted at one apiece.  In the 64th minute, Sam Wood gave Harvey the lead, slipping a shot past Canadians’ goalkeeper Vic Neate. Bob Hannah evened the score two minutes later.


A change of scenery to DePaul Field seemingly provided the impetus for a result in the long-running deadlocked series. Still it was deep into the second half before Hannah scored via a penalty kick. Harvey had a late chance for yet another equalizer, but Neate stopped Wood’s spot-kick.

Canadian Club beat Cleveland Thistle in the Western Final 2-1 at DePaul Field, with Hannah scoring the winner on a penalty kick. But playing away from the friendly confines of the Windy City, they couldn’t grab the prize in the Final, falling 3-0 at Marks Stadium in Rhode Island to Shawsheen FC of Andover, Massachusetts.

1938 National Challenge Cup/Open Cup

February 27, 1938 | Western Semifinal
Sparta Chicago 1 - 0 Maccabees

In what the Chicago Tribune called the biggest local matchup since the Bricklayers closed up shop, the Windy City’s top two teams met in the Western Semifinal in 1938 -- at Sparta Stadium at 21st Street at Kostner Avenue. The matchup between undefeated Sparta and the Maccabees, whose only loss had come in league play to Sparta, proved worthy of the hype.

Munro missed a penalty for Sparta in the first half, leaving the teams to battle for 60 minutes before Jimmy McDermott, who had slipped to the ground on the icy and wet field, managed to kick the ball into the net.

Sparta got past the German Sport Club of Castle Shannon (Pennsylvania) in the Western final before winning Chicago’s first Challenge Cup/Open Cup 6-2 on aggregate over Brooklyn St. Mary’s (both teams pictured at the top of this article).

Charles Cuttone is a writer/author, historian and three-time winner of the National Soccer Coaches Association writing award