Looking at that question you might think the answer is either going to be a game against Tottenham, or a game against Leyton Orient. Or maybe Clapton Orient. Or there again against Tottenham in the first world war when they played on our ground.
But no, let’s get rid of the war time games and restrict ourselves to peacetime. And let me offer up a clue: it was a cup match.
The answer is…
Arsenal against London Caledonians on this day in 1925 in the London FA Challenge Cup. Details are below – and let me confirm, in their day London Cally were a very famous team.
14 September 1891: Billy Heath scored the first ever penalty in a league game for Wolverhampton against Accrington as Wolverhampton won 5-0. In 1893 he joined Arsenal, and scored a hattrick against Walsall Town Swifts on 11 September – Arsenal’s first ever hattrick and Heath’s first goals for the club.
14 September 1901: Alex James born in Lanarkshire. He joined Raith Rovers in 1922 and played almost 100 league games for them before joining Preston NE in 1925.
14 September 1903: Arsenal 4 West Ham 1 (London League – attendance 2000). The 5th straight win at the start of the season with many more to come.
14 September 1918: William Hall and Sir Henry Norris went to Highbury together to see Arsenal beat Millwall Athletic 4-0. The crowd for this second match of the season was only 5,000, but the presence of the directors showed things were getting back to normal in terms of planning for the future.
14 September 1925: Arsenal’s most local derby ever v. London Caledonians in the London FA Challenge Cup; Arsenal a 3-2 win in front of 5000. London Cally played in Caledonian Park, just one mile from Highbury. What’s more, both clubs were formed in 1886. London Caledonians won the Amateur Cup in 1923, and in 1924/5 they won the Isthmian League for the sixth time.
14 September 1923: Doug Lisham born in Birmingham. Having served in the Royal Marine Commandos during the Second World War and taking part in the Walcheren Island landing in Holland he signed as a professional for Walsall in the run up to the return of football after the second world war in August 1946 and in May 1948 moved to Arsenal for £10,500.
14 September 1929: J.J. Williams signed from Stoke City (according to a report in the Arsenal handbook for 1930/1)
14 September 1935: Arsenal had won the league for the last 3 seasons but were struggling to keep up that form. On this day it was Arsenal 2 Sheffield Wednesday 2 with 59,492 in the crowd. Arsenal were 5th.
14 September 1938: Arsenal 1 Derby 2 – third match for Gordon Bremner, a tremendous talent who was tragically, like so many others, lost to the war. It was the only defeat in his first 10 games for the club There were 8 victories and 1 draw.
14 September 1949: Freddie Cox’ Arsenal home debut having signed from Tottenham: – Arsenal 4 WBA 1. Lewis, Goring, Roper and Barnes scored. Freddie went on to play 79 games for Arsenal in the league, scoring nine goals.
14 September 1968: Arsenal 1 Stoke 0 completed seven wins and two draws in the opening nine games. The table made encouraging reading with Arsenal top two points ahead of Leeds.
14 September 1974: 34,596 saw Chelsea 0 Arsenal 0 billed as a “bottom of the table clash”. The press focussed on hooliganism and the campaign by players for freedom on contract. The end of football as we know it was predicted, especially by those journalists not liking an easy story without having to leave the office (or the pub).
14 September 1982: Spartak Moscow beat Arsenal 2-3 in Russia, which looked like a score Arsenal could turn around. However on 29 September Arsenal lost 2-5 at home and Arsenal were out in the first round.
14 September 1991: Crystal Palace 1 Arsenal 4. The start of a run of four successive wins in which Arsenal scored 20 goals, after just 10 in the first seven matches.
14 September 1996: Tony Adams admitted he was an alcoholic. He recovered however to become the first player ever to captain a league winning team in three different decades.
14 September 1999: Fiorentina 0 Arsenal 0. It was the start of the second season of playing Champions League games at Wembley. Arsenal won only one of the games, and the experiment came to an end, although it showed Arsenal could get crowds of over 70,000 when space was available.
14 September 2002: Arsenal beat Charlton 0-3 to continue the unbeaten start to the season. As Double winners the previous season Arsène Wenger said, “We know we can win the league. We know we can be stronger. At this stage last season we were not as good as we are now.” Arsenal did win the cup but came second in the league.
14 September 2004: Arsenal 1 PSV Eindhoven 0 in the first match of the Champions League group stage. Arsenal then drew the next four matches but following a 5-0 win in the final game, topped the group.
14 September 2005: Arsenal’s lowest attendance of the season against Thun in Champions League. Capacity at the Emirates was always reduced for Champions League games due to the demands of Uefa.
14 September 2009: Eduardo’s two match ban for “deceiving the referee” was formally annulled after it was not established that the referee had been deceived. But the precedent of challenging the referee’s decision under media pressure was thus set.
14 September 2013: Arsenal went top of the league after 3-1 away win to Sunderland. Game 9 in the sequence of the all-time record of away wins. Giroud and Ramsey (2) got the goals.