, Arsenal began the league season with a home fixture against Leicester City. , September saw Arsenal win all of their league matches. We only had two and a half days, which is not enough, especially when you are travelling". ", Petit scored a 90th-minute winner for Arsenal against West Ham United and a further win against Chelsea ensured Arsenal finished second, as Leeds and Liverpool failed to win their respective matches.  Arsenal then travelled to Stamford Bridge to face Chelsea.
 Arsenal only managed a draw against Wimbledon on 18 December 1999; Henry's second half goal cancelled out Wimbledon's opener – a cross by Marcus Gayle met Carl Cort, whose shot hit goalkeeper Alex Manninger's left leg and went in.  The equaliser came in the 83rd minute: Kanu received the ball from Overmars, which took him away from goal but hit the ball to the left of De Goey’s dive. For the second consecutive season Arsenal failed to progress past the group stage of the UEFA Champions League; a third-place finish, however, ea… Liverpool 0-0 Arsenal (4-5 pens): Carabao Cup fourth round – as it happened Bernd Leno was man of the match as Arsenal survived 90 minutes before Harry … , Arsenal faced French club Nantes and won the first leg 3–0; Winterburn scored the pick of the three – "a rare but brilliantly struck goal".  Vieira was subsequently charged, banned for six matches and fined a record £45,000 by The Football Association. Defender Steve Bould moved to Sunderland for an estimated fee of £500,000, which ended his 11-year association with Arsenal.  Henry later admitted his failure to score for Arsenal before then was getting him down: "My goal today was very important for me. Wenger said he intended to take the competition seriously given the team's poor UEFA coefficient.
Arsenal went ahead in the 21st minute – Henry beat defender Jonathan Woodgate for pace and scored his 20th goal of the season.  The team then lost to Liverpool at home a week later, who moved into third place.  Manchester United went ahead seven minutes before the end of the first half, but late goals from Kanu and Ray Parlour gave Arsenal victory in the match.  Matthew Upson was forced to come off the pitch before the half-hour mark, after suffering a knee injury. That is something he has not worked on enough in the last two years because he has played more wide, but I think he can become a central striker again. The highest goalscorer was Henry, with 26 goals, followed by Kanu who scored 17 goals.  It was decided on penalties and Arsenal lost after Šuker and Patrick Vieira missed their spot-kicks. For the second consecutive season Arsenal failed to progress past the group stage of the UEFA Champions League; a third-place finish, however, earnt them a consolation place in the UEFA Cup. In October, Arsenal notably staged a comeback against Chelsea, with Nwankwo Kanu scoring a hat-trick in the final 15 minutes of the game. Wenger rested several first-team players to prioritise the 2000 UEFA Cup Final the following week. Henry started the match on the substitutes' bench along with Overmars and Upson, while Šuker was absent as he was unfit. , Amy Lawrence's account of Kanu's impact against Chelsea in The Observer, 24 October 1999. So come February time they will start to feel that pressure – and you don't know what it is like until you have been through it.  In injury time Kanu, in the downpour, chased down the ball and dribbled past the stranded Chelsea goalkeeper on the byline, before curling the ball over Frank Leboeuf and into the far corner of the goal net.
 Arsenal played their home games at Highbury instead of Wembley. "At a Stamford Bridge saturated by drama, he worked his magic when Arsenal looked dead and buried.  The first was against Arsenal at Old Trafford on 24 January 2000.  Wenger conceded afterwards his team were paying for their participation in the UEFA Cup, as "…the recovery time is too short.  Arsenal ended their league campaign against Newcastle United at St James' Park.  Kaba Diawara left Arsenal six months after joining to sign for Marseille. Arsenal used a total of 32 players during the 1999–2000 season and there were 15 different goalscorers.  Arsenal lost 4–2, with Newcastle striker Alan Shearer notably scoring the 300th goal of his career.  Ljungberg and Henry scored for Arsenal in their 2–0 win to put the team third at the end of 1999. After defeat to Aston Villa in December 1998, Arsenal embarked on a 19 match unbeaten run (21 in all competitions) to climb up the league table. Their opening match was a 3–1 win against Second Division Blackpool, where Grimandi, Adams and Overmars got themselves on the scoresheet.  The SEGA Dreamcast name was carried on the home kit, while SEGA was embroidered on the new yellow away kit.  Parlour scored a hat-trick in the return leg – the first of his career. The 1999–2000 season was the 102nd season of competitive football played by Arsenal. A 3–1 away win against Tottenham Hotspur put Arsenal three points clear as United lost to Liverpool on the same night.  In the fourth round, Arsenal faced Leicester City at Highbury. The 1999–2000 season was the 102nd season of competitive football played by Arsenal. , Dixon's late goal earnt Arsenal a point against Aston Villa on 5 March 2000. They didn't play in the FA Cup. Arsenal played out a 3–3 draw against Sheffield Wednesday, which relegated their opponents in the process.  Arsenal recovered three days later to defeat Bradford City by two goals to nil, but lost to Liverpool at Anfield in their final game of August. Kanu and Stefan Malz scored a goal apiece to ensure Arsenal progressed into the fourth round, where they played Middlesbrough away. The club were drawn in Group B, along with Italian club Fiorentina, Barcelona of Spain and Sweden's AIK. The attack was bolstered with the arrival of Titi Camara, Erik Meijer and Vladimír Šmicer.
 In the opening match against Fiorentina, Arsenal dominated possession and created the better chances of the game, but earnt no more than a point after Kanu's late penalty miss.  Rob Hughes of The Times noted his concerns about Arsenal's defence, which: "...conceded 17 goals last season but now, at the halfway stage, [...] have already let in 20", but did go on to add "there was nothing lacking in the tenacity of Arsenal.  The month ended with a 3–1 win against Southampton, in which Bergkamp and Kanu returned to the starting line-up.  After a quiet first half, Leicester scored the opening goal when Neil Lennon's intervention prompted striker Tony Cottee to "gleefully pounce from inside the six-yard box". , The 1999 edition of the FA Charity Shield was contested between Manchester United and Arsenal. Read about Chelsea v Arsenal in the Premier League 1999/00 season, including lineups, stats and live blogs, on the official website of the Premier League. Inconsistent performances in the league, particularly away from home, meant Arsenal never posed a serious threat to Manchester United, the reigning champions.
Numbers in parentheses denote appearances as substitute. , As Arsenal finished third in their Champions League group, they entered the UEFA Cup. So when they came back they had the psychological advantage. Arsenal exited both domestic cup competitions on penalties, being eliminated by Leicester City in a FA Cup fourth round replay and by Middlesbrough at the same stage of the Football League Cup. A confrontation soon after occurred between the player and Neil Ruddock. Wenger selected five midfielders in his starting team, as injuries limited his forward options. Players with number struck through and marked left the club during the playing season. The first came at Valley Parade, away to Bradford City.  Arsenal sought to strengthen the squad's attacking options first by signing Davor Šuker from Real Madrid; the player was prepared to take a pay cut to join the club.  Šuker scored twice against Everton at Highbury on 16 October 1999.
 A week after the team faced Manchester United at Highbury. ", Together with the other clubs playing in European competitions, Arsenal entered the Football League Cup in the third round.  United midfielder Roy Keane scored twice to overturn Arsenal's 41st-minute lead and inflict the home team's first defeat since December 1997. ", In the lead up to the final against Galatasaray in Copenhagen, scuffles took place between British and Turkish supporters at City Hall Square after an Arsenal fan was stabbed. Leicester goalkeeper Pegguy Arphexad blocked Dixon and Grimandi's spot-kicks to help his side win.  Arsenal beat Watford and continued their strong finish to the season with a 1–0 win at Everton to move into second place. Dixon, Nigel Winterburn and Overmars were rested for the match, replaced by Oleh Luzhny, Slyvinho and Davor Šuker. Six Arsenal players were sent off during the season: Vieira, Keown, Henry, Grimandi (twice) and Luzhny. , Frenchman Rémi Garde retired from career football at the end of the 1998–99 season. , In spite of playing the second half against Wimbledon with ten men after the dismissal of Luzhny, Arsenal defeated their London rivals by three goals to one. The break was good for them because at the same time we dropped points and so did the other teams. They were exposed and didn't get any protection. After a disappointing seventh-place finish the previous season, which left Liverpool without even UEFA Cup qualification, manager Gérard Houllier began to rebuild his squad and made seven close season signings. In April Arsenal moved to the top of the Premier League after beating Middlesbrough 6–1, albeit having played a match more than Manchester United.
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