Every competitive match Arsenal played in 1999–00 — 58 matches, 32 won, 14 drawn, 12 lost, with scorers and attendances where the record holds them.
| Date | Competition | Venue | Opponent | Their season | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 7 Aug 1999 | Premier League | H | Leicester City | Leicester City 1999–00 | 2–1 | Dennis Bergkamp 65, Trevor Sinclair 90 | 38,026 |
| 10 Aug 1999 | Premier League | A | Derby County | Derby County 1999–00 | 2–1 | Emmanuel Petit 40, Dennis Bergkamp 47 | 25,901 |
| 14 Aug 1999 | Premier League | A | Sunderland | Sunderland 1999–00 | 0–0 | 41,680 | |
| 22 Aug 1999 | Premier League | H | Manchester United | Manchester United 1999–00 | 1–2 | Freddie Ljungberg 41 | 38,147 |
| 25 Aug 1999 | Premier League | H | Bradford City | Bradford City 1999–00 | 2–0 | Patrick Vieira 8, Nwankwo Kanu 17 | 38,073 |
| 28 Aug 1999 | Premier League | A | Liverpool | Liverpool 1999–00 | 0–2 | 44,886 | |
| 11 Sep 1999 | Premier League | H | Aston Villa | Aston Villa 1999–00 | 3–1 | Davor Šuker 45, Davor Šuker 49, Nwankwo Kanu 82 | 38,093 |
| 14 Sep 1999 | Champions League | A | ACF Fiorentina | 0–0 | 33,903 | ||
| 18 Sep 1999 | Premier League | A | Southampton | Southampton 1999–00 | 1–0 | Thierry Henry 79 | 15,242 |
| 22 Sep 1999 | Champions League | N | AIK Fotboll | 3–1 | Freddie Ljungberg 28, Thierry Henry 90+1, Davor Šuker 90+3 | 71,227 | |
| 25 Sep 1999 | Premier League | H | Watford | Watford 1999–00 | 1–0 | Nwankwo Kanu 86 | 38,127 |
| 29 Sep 1999 | Champions League | A | Barcelona | 1–1 | Nwankwo Kanu 81 | 87,574 | |
| 3 Oct 1999 | Premier League | A | West Ham United | West Ham United 1999–00 | 1–2 | Davor Šuker 77 | 26,009 |
| 12 Oct 1999 | League Cup | H | Preston North End | Preston North End 1999–00 | 2–1 | Nwankwo Kanu 31, Stefan Malz 61 | 15,239 |
| 16 Oct 1999 | Premier League | H | Everton | Everton 1999–00 | 4–1 | Lee Dixon 40, Davor Šuker 54, Davor Šuker 61, Nwankwo Kanu 90 | 38,042 |
| 19 Oct 1999 | Champions League | N | Barcelona | 2–4 | Dennis Bergkamp 44, Marc Overmars 85 | 73,091 | |
| 23 Oct 1999 | Premier League | A | Chelsea | Chelsea 1999–00 | 3–2 | Nwankwo Kanu 75, Nwankwo Kanu 83, Nwankwo Kanu 90 | 34,958 |
| 27 Oct 1999 | Champions League | N | ACF Fiorentina | 0–1 | 73,336 | ||
| 30 Oct 1999 | Premier League | H | Newcastle United | Newcastle United 1999–00 | 0–0 | 38,106 | |
| 2 Nov 1999 | Champions League | A | AIK Fotboll | 3–2 | Marc Overmars 17, Marc Overmars 52, Davor Šuker 56 | 33,005 | |
| 7 Nov 1999 | Premier League | A | Tottenham Hotspur | Tottenham Hotspur 1999–00 | 1–2 | Patrick Vieira 38 | 36,085 |
| 20 Nov 1999 | Premier League | H | Middlesbrough | Middlesbrough 1999–00 | 5–1 | Marc Overmars 26, Dennis Bergkamp 40, Dennis Bergkamp 49, Marc Overmars 61, Marc Overmars 78 | 38,082 |
| 25 Nov 1999 | UEFA Cup | H | Nantes | 3–0 | Marc Overmars 13, Nigel Winterburn 81, Dennis Bergkamp 90 | 36,618 | |
| 28 Nov 1999 | Premier League | H | Derby County | Derby County 1999–00 | 2–1 | Thierry Henry 11, Thierry Henry 51 | 37,964 |
| 30 Nov 1999 | League Cup | A | Middlesbrough | Middlesbrough 1999–00 | 2–2 | Thierry Henry 38, Davor Šuker 80 | 23,157 |
| 4 Dec 1999 | Premier League | A | Leicester City | Leicester City 1999–00 | 3–0 | Gilles Grimandi 23, Lee Dixon 53, Marc Overmars 75 | 20,495 |
| 9 Dec 1999 | UEFA Cup | A | Nantes | 3–3 | Gilles Grimandi 25, Thierry Henry 31, Marc Overmars 42 | 17,000 | |
| 13 Dec 1999 | FA Cup | H | Blackpool | Blackpool 1999–00 | 3–1 | Gilles Grimandi 24, Tony Adams 65, Marc Overmars 90 | 34,143 |
| 18 Dec 1999 | Premier League | H | Wimbledon | Wimbledon 1999–00 | 1–1 | Thierry Henry 61 | 38,052 |
| 26 Dec 1999 | Premier League | A | Coventry City | Coventry City 1999–00 | 2–3 | Freddie Ljungberg 67, Davor Šuker 86 | 22,757 |
| 28 Dec 1999 | Premier League | H | Leeds United | Leeds United 1999–00 | 2–0 | Ljunberg 32, Thierry Henry 58 | 38,096 |
| 3 Jan 2000 | Premier League | A | Sheffield Wednesday | Sheffield Wednesday 1999–00 | 1–1 | Emmanuel Petit 40 | 26,155 |
| 9 Jan 2000 | FA Cup | H | Leicester City | Leicester City 1999–00 | 0–0 | 35,710 | |
| 15 Jan 2000 | Premier League | H | Sunderland | Sunderland 1999–00 | 4–1 | Thierry Henry 3, Davor Šuker 28, Davor Šuker 33, Thierry Henry 81 | 38,039 |
| 19 Jan 2000 | FA Cup | A | Leicester City | Leicester City 1999–00 | 0–0 | 15,235 | |
| 24 Jan 2000 | Premier League | A | Manchester United | Manchester United 1999–00 | 1–1 | Freddie Ljungberg 11 | 58,293 |
| 5 Feb 2000 | Premier League | A | Bradford City | Bradford City 1999–00 | 1–2 | Thierry Henry 13 | 18,276 |
| 13 Feb 2000 | Premier League | H | Liverpool | Liverpool 1999–00 | 0–1 | 38,098 | |
| 26 Feb 2000 | Premier League | H | Southampton | Southampton 1999–00 | 3–1 | Freddie Ljungberg 22, Dennis Bergkamp 36, Freddie Ljungberg 69 | 38,044 |
| 2 Mar 2000 | UEFA Cup | H | Deportivo de La Coruña | 5–1 | Lee Dixon 5, Thierry Henry 30, Thierry Henry 67, Nwankwo Kanu 78, Dennis Bergkamp 83 | 37,837 | |
| 5 Mar 2000 | Premier League | A | Aston Villa | Aston Villa 1999–00 | 1–1 | Lee Dixon 84 | 36,930 |
| 9 Mar 2000 | UEFA Cup | A | Deportivo de La Coruña | 1–2 | Thierry Henry 63 | 25,000 | |
| 12 Mar 2000 | Premier League | A | Middlesbrough | Middlesbrough 1999–00 | 1–2 | Dennis Bergkamp 70 | 34,244 |
| 16 Mar 2000 | UEFA Cup | H | SV Werder Bremen | 2–0 | Thierry Henry 21, Freddie Ljungberg 77 | 38,009 | |
| 19 Mar 2000 | Premier League | H | Tottenham Hotspur | Tottenham Hotspur 1999–00 | 2–1 | Chris Armstrong 20, Thierry Henry 45 | 38,131 |
| 23 Mar 2000 | UEFA Cup | A | SV Werder Bremen | 4–2 | Ray Parlour 8, Ray Parlour 25, Thierry Henry 59, Ray Parlour 70 | 33,000 | |
| 26 Mar 2000 | Premier League | H | Coventry City | Coventry City 1999–00 | 3–0 | Thierry Henry 50, Gilles Grimandi 79, Nwankwo Kanu 80 | 38,027 |
| 1 Apr 2000 | Premier League | A | Wimbledon | Wimbledon 1999–00 | 3–1 | Nwankwo Kanu 33, Nwankwo Kanu 41, Thierry Henry 89 | 25,858 |
| 6 Apr 2000 | UEFA Cup | H | RC Lens | 1–0 | Dennis Bergkamp 2 | 38,102 | |
| 16 Apr 2000 | Premier League | A | Leeds United | Leeds United 1999–00 | 4–0 | Thierry Henry 21, Martin Keown 70, Nwankwo Kanu 82, Marc Overmars 90 | 39,307 |
| 20 Apr 2000 | UEFA Cup | A | RC Lens | 2–1 | Thierry Henry 41, Nwankwo Kanu 87 | 41,043 | |
| 23 Apr 2000 | Premier League | A | Watford | Watford 1999–00 | 3–2 | Thierry Henry 18, Ray Parlour 43, Thierry Henry 45 | 19,670 |
| 29 Apr 2000 | Premier League | A | Everton | Everton 1999–00 | 1–0 | Marc Overmars 34 | 35,919 |
| 2 May 2000 | Premier League | H | West Ham United | West Ham United 1999–00 | 2–1 | Marc Overmars 69, Emmanuel Petit 90 | 38,093 |
| 6 May 2000 | Premier League | H | Chelsea | Chelsea 1999–00 | 2–1 | Thierry Henry 21, Thierry Henry 48 | 38,119 |
| 9 May 2000 | Premier League | H | Sheffield Wednesday | Sheffield Wednesday 1999–00 | 3–3 | Lee Dixon 34, Sylvinho 78, Thierry Henry 79 | 37,271 |
| 14 May 2000 | Premier League | A | Newcastle United | Newcastle United 1999–00 | 2–4 | Nwankwo Kanu 7, Stefan Malz 53 | 36,450 |
| 17 May 2000 | UEFA Cup | A | Galatasaray S.K. | 0–0 | 38,919 |
110 of the goals in this season carry a named scorer.
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