The 1926–27 season was the 26th season of competitive football played by Cardiff City F.C. and the team's sixth consecutive season in the First Division of the Football League. Having finished 16th the previous season, Fred Stewart made reshaped his squad but endured a slow start to the campaign. However, led by the goals of top scorer Hughie Ferguson, the club eased away from the relegation zone after the midway point of the campaign and finished in 14th position.

In the FA Cup, Cardiff beat Aston Villa and Darlington before overcoming reigning holders Bolton Wanderers. They required a replay to beat Chelsea in the quarter-finals and defeated Reading in the semi-final to reach their second FA Cup final in three years. In the final, Cardiff defeated Arsenal via a single goal from Ferguson. In doing so, they became the only team from outside England to have won the FA Cup in the competition's history. Cardiff also won the Welsh Cup for the fifth time in their history, beating Rhyl 2–0 in the final and achieving a unique feat of winning two national Cup competitions from different countries in the same season.

Billy Hardy made the most appearances for the club during the season with 52 in all competitions. Ferguson set a new club record with 32 goals in all competitions which stood until 2003 when Robert Earnshaw scored a total of 35. His tally of 26 in the league was also a club record which stood until 1947. The economic downturn in the South Wales area led to a drop in attendance figures with only three league matches at Ninian Park attracting more than 20,000 spectators.

Background Cardiff City had joined the Football League in 1920, entering the Second Division and winning promotion to the First Division in their first season. The club had come close to becoming the first team from outside England to win the First Division in 1923–24, losing the title on the final day of the season to Huddersfield Town on goal average. Two years later, Cardiff became the first Welsh side to reach an FA Cup final, playing in the 1925 final in which they lost 1–0 to Sheffield United. Such was the competitiveness of the side at the time that The Times labelled the team as "perhaps the best team in the country". These near misses with competition victories had raised hopes of a first trophy success in English football for the 1925–26 campaign. However, the team struggled to adapt to a new change in the offside law that had reduced the number of defenders between an attacking player and the goal from three to two. The change was an attempt to increase the number of goals being scored and, although the new rule had the desired effect (the goals per game average jumped by over 1, from 2.58 to 3.69), Cardiff struggled under the new format.

By October 1925 Cardiff were bottom of the First Division table, leading manager Fred Stewart to implement several changes to the squad. As well as dropping some first team players he signed three new forwards, Joe Cassidy from Bolton Wanderers, George McLachlan from Clyde and Hughie Ferguson from Motherwell. The £3,800 spent on Cassidy was a new club transfer record before Stewart broke the record again to sign Ferguson for £5,000. The trio provided fresh impetus in the squad and Ferguson's 19 league goals proved instrumental in helping the side avoid relegation and finish the campaign in 16th position.

Following the below par performances, Stewart initiated an overhaul of his playing squad during the off-season. The high-profile departures included Jack Evans, the club's first professional signing in 1910 who had been with the side for 16 years. Also leaving were Cassidy, less than a year after his £3,800 move and for a fee described in The Times as "substantially less" than the one paid for him, and Joe Nicholson, who had led the club's attack in the 1925 FA Cup Final. Several fringe players also left the club, including Herbie Evans, Alfie Hagan, Joe Hills, Denis Lawson, Jack Page and Ebor Reed. However, the most significant departure was club captain Jimmy Blair who joined A.F.C. Bournemouth for £3,900. His sale resulted in Fred Keenor being appointed the new captain of the first team. He had served as vice-captain under Blair and had filled the role on numerous occasions and was a popular choice for the position. Upon his appointment, the Football Echo remarked that Keenor was "a leader in every sense of the word, he commands respect of colleagues and sets an inspiring example by his wholehearted enthusiasm."

To compensate for the departures, Stewart made several signings for the first team. However, none of the transfers arriving were of a similar cost to the previous season's arrivals. As part of Cassidy's move to Dundee, Sam Irving moved to Cardiff. Ernie Curtis was signed from local amateur side Cardiff Corinthians while Tom Pirie from Aberdeen and Jim Baillie from Derry Celtic were also signed from the Scottish leagues. Goalkeeper Tom Wainwright was signed from non-League side Boston Town as back-up to Tom Farquharson after attracting attention in the team's FA Cup run the previous year. The most high-profile signing was the arrival of England international George Blackburn from Aston Villa in a swap deal with Nicholson. A change was also initiated at boardroom level with Syd Nicholls stepping down as chairman to be replaced by Walter Parker.

The season was preceded by the 1926 general strike, a protest against wage reductions and worsening work conditions for coal miners. Although the strike itself lasted for only nine days, some miners held out for several months as other industries returned to work. Coal mining was a major industry in the South Wales Valleys, a region where Cardiff drew a significant portion of its fanbase, and the collapse of the industry led to decreased ticket sales for the club. A standing ticket at one of the club's home fixtures cost one shilling, 10 per cent of a miner's daily pay at the time. The halt in production and declining sales of British industrial goods also affected Cardiff Docks, another prominent portion of the club's fanbase, which reduced its workforce. In an effort to lessen the impact on the club, Cardiff Council began operating a tram service directly to the ground.

First Division August–December Cardiff began the campaign with an away match against Burnley on 28 August. The match was a highscoring affair; Ferguson, Cardiff's top goalscorer the previous year, opened his account with a brace and Len Davies added a third. However, Burnley scored four to take the opening day victory. Cardiff claimed their first point of the season two days later with a goalless draw with Leeds United. The side played their first home fixture on 4 September and worries over attendance figures due to the economic downturn in South Wales proved unfounded as more than 19,000 spectators attended a match against West Bromwich Albion. Some reports noted that fans were walking up to 20 miles to attend fixtures in order to save money on train fares. Len Davies scored his side's goal in a 1–1 draw. In the return fixture against Leeds on 6 September, Cardiff recorded their first win of the campaign with a 3–1 victory, Potter Smith and Willie Davies scored their first goals of the campaign while Ferguson added a third.

Results soon began to deteriorate in September. Despite a brace from Ferguson, Cardiff suffered a 3–2 home defeat to Aston Villa and this was followed a 2–0 defeat against Bolton Wanderers. Despite a 1–1 draw with Newcastle United on 20 September, Stewart initiated changes for a home match against Manchester United five days later, handing debuts to new signings Baillie, Curtis and Pirie and bringing in Tom Sloan for his first appearance of the season. The changes proved ineffectual however and Cardiff fell to a 2–0 defeat. The only one of Stewart's debutants to retain their place for the following match was 19-year-old Curtis, who scored his first goal for the club in a 6–3 defeat to fellow strugglers Derby County. Cardiff had been leading the match 3–2 at half time and The Times remarked that they looked the more likely to continue scoring at the start of the second half. However, when Derby equalised through a cross-shot, Cardiff's previous good efforts deserted them and Derby ran out winners, leaving Cardiff one place above the relegation zone.

A 3–0 victory over mid-table side Sheffield United on 9 October lifted Cardiff two places, Willie Davies, Irving and Ferguson with the goals. A goalless draw with Huddersfield preceded a three-match winning run that lifted the club to mid-table by the start of November. Cardiff opened with a 3–0 victory over Sunderland with a brace from Ferguson and one from Curtis. Bury were beaten 3–2 a week later, despite Keenor and Willie Davies missing the game on international duty. Another brace from Ferguson and McLachlan's first goal of the season secured victory. A 1–0 win over Birmingham on 6 November secured Cardiff's fourth win in five matches but the game was watched by a crowd of just over 10,000, the lowest home crowd of the year as early season optimism faded. Cardiff's winning run was brought to an end by a 4–1 defeat to Tottenham Hotspur on 13 November, the first time they had lost at White Hart Lane.

The return fixture against West Ham resulted in a 2–1 defeat soon after and Cardiff were dealt a further blow as Willie Davies made his final appearance of the season as he was ruled out indefinitely after contracting pleurisy and confined to a sanatorium. Cardiff's next fixture against Sheffield Wednesday was delayed for two days owing to heavy fog in the Yorkshire area. When the two teams did meet, Cardiff were beaten 3–0. The side's first win in more than a month, a 1–0 victory over fellow strugglers Everton lifted the side above the relegation zone. Concerned about his team's faltering performances, Stewart made several more additions to his squad in December, adding goalkeeper Tommy Hampson from Darlington and forwards Fred Castle and Frank Matson from Mid Rhondda and Reading respectively. Matson made his debut against Blackburn Rovers on 18 December and Castle against Newcastle a week later, but neither were able to stop the side falling to 1–0 and 5–0 defeats. Cardiff ended the calendar year with a 2–0 win over Arsenal following goals from Ferguson and Curtis. The match attracted the largest home crowd for a league fixture of the season with more than 25,000 in attendance.

January–May Cardiff began the new calendar year with the reverse fixture against Arsenal on New Year's Day. Arsenal twice took the lead through Jimmy Brain but Cardiff equalised each time, first from Curtis and then by Len Davies. However, Brain completed his hat-trick to secure victory for his side and leave Cardiff one place above the relegation zone. Due to FA Cup commitments, Cardiff played only two further matches in the month, against Burnley on 15 January and Aston Villa on 31 January, with both matches ending in goalless draws. The results left Cardiff one point above the relegation zone, although they held three games in hand over 19th place Everton. During this period, a mixture of injury and poor form had seen the newly appointed captain Keenor dropped from the side. Frustrated at his lack of playing time over the Christmas and New Year period, he handed in a transfer request which was accepted at a board meeting on 19 January. Third Division South side Bristol Rovers opened talks over the transfer but the move ultimately collapsed.