April 6, 1931: Arsenal clinch the title of the old Football League Division 1 (hereafter referred to as "the League"), with a draw against Portsmouth of Hampshire, 1-1 at the Arsenal Stadium, a.k.a. Highbury, North London. The Yankees were working their way north from Spring Training, and did not play an official game.
April 22, 1933: Arsenal clinch the League, beating Chelsea of West London, 3-1 at Chelsea's ground, Stamford Bridge. The Yankees beat the Red Sox, 2-1 at Fenway Park in Boston.
April 28, 1934: Arsenal clinch the League, with a draw against Chelsea, 2-2 at Stamford Bridge. The Yankees lose to the Red Sox, 4-2 at Yankee Stadium.
April 20, 1935: Arsenal clinch the League, beating Huddersfield 1-0 at Highbury. The Yankees beat the Philadelphia Athletics (now the Oakland Athletics), 3-1 at Yankee Stadium.
April 25, 1936: Arsenal win the FA Cup, beating Sheffield United of Yorkshire, 1-0 at Wembley. The Yankees lose to the Red Sox, 7-2 at Fenway.
May 7, 1938: Arsenal clinch the League, beating Bolton Wanderers of Lancashire, 5-0 at Highbury. The Yankees beat the Detroit Tigers, 12-8 at Yankee Stadium.
April 10, 1948: Arsenal clinch the League, with a draw against Huddersfield at their ground, Leeds Road, 1-1. The Yankees were working their way north from Spring Training, and did not play an official game.
April 29, 1950: Arsenal win the FA Cup, beating Merseyside club Liverpool, 2-0 at Wembley. The Yankees beat the Washington Senators (now the Minnesota Twins), 6-2 at Griffith Stadium in Washington.
May 1, 1953: Arsenal clinch the League, beating Burnley of Lancashire, 3-2 at Highbury. The Yankees lost to the Chicago White Sox, 6-5 at Comiskey Park in Chicago.
April 28, 1970: Arsenal win the Inter-Cities Fairs Cup (the tournament now known as the Europa League), beating Anderlecht of Brussels, Belgium, 3-0 at Highbury. The Yankees beat the California Angels (the team now known as the Los Angeles Angels of Anaheim), 7-5 at Yankee Stadium.
May 3, 1971: Arsenal clinch the League, beating their North London arch-rivals, Tottenham Hotspur, 1-0 at Spurs' ground, White Hart Lane. The Yankees were not scheduled to play that day.
May 8, 1971: Arsenal win the FA Cup, clinching "The Double," beating Liverpool, 2-1 in extra time at Wembley. The Yankees beat the White Sox, 2-1 at Comiskey.
May 12, 1979: Arsenal win the FA Cup, beating Manchester United, 3-2 at Wembley. The Yankees beat the Angels, 6-5 at Yankee Stadium.
April 5, 1987: Arsenal win the Football League Cup, beating Liverpool, 2-1 at Wembley. The Yankees opened their regular season the next day.
May 26, 1989: Arsenal clinch the League, beating Liverpool, 2-0 at Liverpool's ground, Anfield. The way the tiebreakers worked, Arsenal had to beat Liverpool by 2 goals, and got the 2nd from Michael Thomas in the last minute of the last game of the season. The Yankees lost to the Oakland Athletics (a.k.a. the A's), 4-0 at Yankee Stadium.
May 6, 1991: Arsenal clinch the League, beating Manchester United, 3-1 at Highbury. Actually, they clinched earlier in the day, without playing, when Liverpool lost to Nottingham Forest. The next season was the last for the old Football League Division One; thereafter, it would be the Premier League (again, herefore referred to as "the League"). The Yankees lost to the Seattle Mariners, 4-2 at Yankee Stadium.
April 18, 1993: Arsenal win the League Cup, beating Sheffield Wednesday of Yorkshire, 2-1 at Wembley. The Yankees lost to the Texas Rangers, 12-2 at Yankee Stadium.
May 20, 1993: After the Final ended 1-1 5 days earlier, Arsenal play Sheffield Wednesday again, in a replay, and again win 2-1 at Wembley. The Yankees were not scheduled to play that day.
May 4, 1994: Arsenal win the European Cup Winners' Cup, beating Parma of Italy, 1-0 at Parken Stadium in Copenhagen, Denmark. The Yankees lost to the Angels, 7-6 at Yankee Stadium.
May 3, 1998: Arsenal clinch the League, beating Everton of Merseyside, 4-0 at Highbury. The Yankees beat the Kansas City Royals, 10-1 at Kauffman Stadium in Kansas City.
May 16, 1998: Arsenal win the FA Cup, and the Double, beating North-East club Newcastle United, 2-0 at Wembley. The Yankees beat the Minnesota Twins, 5-2 at Yankee Stadium. The next day, while Arsenal were having their victory parade, David Wells pitched a perfect game for the Yankees against the Twins.
May 4, 2002: Arsenal win the FA Cup, beating Chelsea, 2-0 at the Millennium Stadium in Cardiff, Wales. This was the seat of the Final between the 2000 closing of the old Wembley and the 2007 opening of the new one. The Yankees lost to the Mariners, 6-5 at Yankee Stadium.
May 8, 2002: Arsenal clinch the League, and the Double, beating Manchester United, 1-0 at United's ground, Old Trafford. The Yankees beat the Tampa Bay Devil Rays (now known as the Tampa Bay Rays), 7-2 at Tropicana Field in St. Petersburg.
May 17, 2003: Arsenal win the FA Cup, beating Southampton of Hampshire, 1-0 at the Millennium Stadium. The Yankees lost to the Rangers, 5-2 at Yankee Stadium.
April 25, 2004: Arsenal clinch the League, with a draw against Spurs, 2-2 at White Hart Lane. Arsenal had now won the League at White Hart Lane as many times as Spurs had: 2. The Yankees also played their arch-rivals, the Red Sox, and weren't so lucky, losing 2-0 at Yankee Stadium.
May 21, 2005: Arsenal win the FA Cup, after drawing with Manchester United, 0-0, despite being down to 10 men, beating them 5-4 on penalty kicks, at the Millennium Stadium. The Yankees weren't so lucky, losing an Interleague game to the New York Mets, 7-1 at Shea Stadium in Queens.
May 17, 2014: Arsenal win the FA Cup, beating Hull City of Yorkshire, 3-2 in extra time, at the new Wembley Stadium in London. The Yankees won an Interleague game against the Pittsburgh Pirates, 7-1 at the new Yankee Stadium in The Bronx.
May 30, 2015: Arsenal win the FA Cup, beating Aston Villa of Birmingham, 4-0 at Wembley. The Yankees beat the A's, 5-3 at the Oakland Coliseum.
May 27, 2017: Arsenal win the FA Cup, beating Chelsea, 2-1 at Wembley. The Yankees beat the A's, 3-2 at Yankee Stadium.
Overall: The Yankees have won 14 games on days when The Arsenal have won trophies, lost 11, and were not scheduled to play on 5 such days.
UPDATE: The 2020 FA Cup Final was delayed until August 1, due to COVID restrictions. Arsenal beat Chelsea, 2-1 at Wembley. The Yankees beat the Red Sox, 5-2 at Yankee Stadium.
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