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Overmars signed for Arsenal in June 1997.
the fee was reported to be between £5 million and £7 million, with the player on a five-year contract, paid £18,000 per week. Overmars relished the challenge of playing in England: "I like English football because there is more pace. With my speed and quality I think it will be good for me here."
Arsène Wenger, the manager of Arsenal believed Overmars had his "best years ahead of him" and met his criteria of a player "used to the pressures of playing for a big club and everything that goes with it." He opined that Arsenal lost the Premier League at home the previous season – "we were maybe the best away team," and commented on their inability to play expansive football. Wenger felt the signing of Overmars would rectify that problem.
Overmars made his competitive debut for Arsenal against Leeds United in a 1–1 draw on 9 August 1997. Two weeks later, he scored his first goal for the club, away to Southampton. Arsenal went to the top of the league table on goal difference in September 1997, after a 4–0 win against West Ham United. Overmars, who scored two goals in the match, had now "run into devastating form" according to Brian Glanville. His impact however waned in the subsequent months and so did Arsenal's form; a 3–1 defeat to Blackburn Rovers on 13 December 1997 meant the club dropped to fifth place. The turn of the year saw improvement to Overmars' game, which coincided with "the more general rejuvenation of the whole team." He scored both of Arsenal's goals in their win over Leeds United on 11 January 1998. Overmars up until this point was subject to criticism from commentators and fans. Wenger emphasised that this was his first year in England and there was more to come from him. He said Overmars was a "positive buy" and pointed out that his goalscoring record was "not bad for a winger."
Arsenal caught up with league leaders Manchester United by the time both clubs played each other at Old Trafford in March 1998. Overmars was a constant threat in the match and scored in the 80th minute. He received the ball from Nicolas Anelka and ran with it, before managing to flick it beyond the goalkeeper, Peter Schmeichel. Arsenal went on to win, which put them six points behind Manchester United, with three games in hand. Overmars afterwards said: "This was a great result for us. But you don't win the Premier League against Manchester United; you have to beat the other clubs." Arsenal overtook Manchester United in April 1998, and won the league after beating Everton on 3 May 1998; Overmars scored two goals in the match. The team later faced Newcastle United in the 1998 FA Cup Final and it was Overmars who scored the opening goal, in the 23rd minute. Anelka's goal in the second half ensured victory and completed a league and cup double for Arsenal. Wenger praised Overmars after the final:
"All Europe thought Overmars was dead because of his damaged knee, but in every important game we have had this season, he has scored. He has got great mental strength. He is a world-class player."
Overmars began the 1998–99 season for Arsenal in good form; he scored against Manchester United in the 1998 FA Charity Shield and in the team's opening game of the league campaign, at home to Nottingham Forest. Arsenal participated in the Champions League, but their time in the competition was brief. The team did not make it past the group stage, and in the decisive game against Dynamo Kyiv which they lost, Overmars was ruled out with an abdominal injury. In February 1999, he scored a "controversial" winning goal against Sheffield United in the FA Cup fifth round. Nwankwo Kanu failed to return the ball to the opposition, in order to allow one of their players to receive treatment for an injury. Due to the controversial circumstances in which the game was won, Wenger immediately offered a replay. His proposal was accepted by The Football Association and Arsenal went on to win the replayed match 2–1, where the opening goal was scored by Overmars. Arsenal exited the competition in the semi-final stage against Manchester United, who went on to win the league.
In November 1999, he scored his first hat-trick for Arsenal, at home to Middlesbrough. His performance was lauded by journalist Lynne Truss, who wrote in The Times: "Overmars was in top Jack Russell form, bounding after the ball and prepared to savage anybody who tried to take it away from him."He twisted his ankle in action for Arsenal against Sheffield Wednesday in January 2000 and was out of action for six weeks. Unlike the previous two seasons, Arsenal never did pose a serious threat to Manchester United, who went on to retain the league in 1999–2000. Overmars had suggested before the campaign that Arsenal were as strong as their rivals, "especially in attack where we now have so many more options." Arsenal ended the league season strongly, winning eight games in a row between March and May to move from fifth to second place. In April 2000, Overmars scored the winning goal against Everton and was the standout performer in the game. His final game for Arsenal was the 2000 UEFA Cup Final against Galatasaray, which they lost 4–1 on penalties after a goalless draw.
In 2008, Overmars was voted as the twelfth-greatest player in Arsenal's history by the club's supporters.