The team immediately improved under Wenger's management, coming third and winning a UEFA Cup place in 1996–97, missing out on second (and a Champions League spot) on goal difference. Wenger rebuilt the Arsenal squad with a crop of French players who were seemingly unknown in the UK. Patrick Vieira had been signed on Wenger's recommendation before he had officially taken up the reins, and Wenger added Nicolas Anelka and Emmanuel Petit, as well as Dutch winger Marc Overmars in the summer of 1997. Wenger melded the new arrivals with some of the "old guard", retaining Adams, Dixon, Winterburn, Keown and Bould, and he kept Pat Rice on as assistant manager.
Wenger got his first silverware, and became the first foreign manager to win the English league, the following season, when he steered the side to their second double. It had looked like Arsenal were out of the title race by December after losing 3–1 at home to Blackburn, but they overcame a twelve point deficit to overtake Manchester United; a 4–0 home win over Everton on 3 May won the title with two matches to spare. On 16 May, Arsenal beat Newcastle United 2–0 in the FA Cup final to complete the double. To top it off, the same season Ian Wright broke Cliff Bastin's goalscoring record, bringing his tally to 185 goals before leaving the club in the summer of 1998.
Despite the signing of Fredrik Ljungberg in 1998 and Thierry Henry a year later, a more barren period followed for Arsenal over the next few years, though they came close several times. Arsenal led the League for much of 1998–99, until a 1–0 loss to Leeds United allowed Manchester United to overtake them; Arsenal beat Aston Villa on the last day of the season but United's victory over Spurs meant they took the title. To rub it in further, Arsenal also lost the last ever FA Cup semi-final replay to Manchester United; Dennis Bergkamp had missed a penalty in normal time, and Ryan Giggs scored the winner in extra time after a mazy solo run through the Arsenal defence. Arsenal's return to the Champions League for the first time in seven years was also unsuccessful, as they failed to get past the group stage.
Arsenal came second again in 1999–2000; this time, there was never any real title race and Arsenal finished the season 18 points behind winners Manchester United. Arsenal had another poor season in the Champions League, finishing third in their group; this won them a consolation place in the UEFA Cup, and Arsenal got all the way to the final, where they faced Galatasaray in Copenhagen, the scene of their 1994 Cup Winners' Cup triumph. The match was a tepid affair, a 0–0 draw with few chances; it went to penalties and Arsenal lost after Davor Šuker and Patrick Vieira missed their spot-kicks.
Arsenal again finished second in 2000–01, this time ten points behind Manchester United; the title race had been as good as over since February, when Arsenal lost 6–1 at Old Trafford. Arsenal's season gave priority to the Cups and Europe. They beat Spurs in the semi-finals and met Liverpool in the final at the Millennium Stadium, Cardiff; Arsenal dominated most of the match, and were denied a goal by the arm of defender Stephane Henchoz, which went unpunished. Arsenal finally did go 1–0 up through Ljungberg but succumbed to two late Michael Owen goals and lost 2–1. In Europe, Arsenal made it to the Champions League quarter-finals for the first time since 1972, only to be eliminated on the away goals rule by eventual finalists Valencia.
By now Wenger had been forced to rebuild much of the Double-winning side of 1998; Anelka, Overmars and Petit had all left for Spanish clubs in return for hefty fees, while age was finally catching up with the famous back line; Bould and Winterburn had already left, and Adams and Dixon would only last another season before retiring. In their place, Wenger signed the likes of Sol Campbell and Lauren in defence, as well as promoting Ashley Cole from the youth ranks. In midfield, Wenger added the talismanic Robert Pirès and signed his compatriot Sylvain Wiltord in attack, while in the meantime Thierry Henry had adapted to the English game to become one of the Premiership's best strikers.
Attack was definitely Arsenal's forté as they won a record-equalling third Double in 2001–02 season; the Gunners were the only team to score in every game of the Premiership season, and went unbeaten in domestic away games. After an initially tight title race (just three points separated the top four in February), Arsenal pulled away from the pack with a 13-game winning streak, finishing seven points ahead of runners-up Liverpool. Arsenal secured the title in the penultimate game of the season with a 1–0 win over Manchester United at Old Trafford, the goal coming from Wiltord. The previous weekend, Arsenal had wrapped up their eighth FA Cup, beating Chelsea 2–0 with goals from Ray Parlour and Freddie Ljungberg.
In 2002–03, Arsenal became the first club in more than 20 years to retain the FA Cup, with a 1–0 victory against Southampton thanks to a Pirès goal. Their joy was soured by the fact that they narrowly missed out on retaining the Premiership title. Arsenal had led eventual winners Manchester United by eight points at one stage, but their form collapsed late on in the season; they drew 2–2 away to Bolton Wanderers after leading 2–0, and then lost 3–2 at home to Leeds United a week later, which gave United the title.
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