11. Alex Manninger
Manninger signed for Arsenal as David Seaman’s understudy in 1997, and went on to make 64 appearances during his five years at the club. With Seaman injured during his debut campaign, the Austrian covered and kept clean sheets in six consecutive games, the last of which came in a 1-0 win at Manchester United. His performances earned him the Premier League Player of the Month award in March 1998.
Manninger left Arsenal for Espanyol in 2002 and, after brief spells at various European sides, he surprisingly joined Liverpool in July 2016. The shot-stopper announced his retirement a year later, hanging up his gloves without ever playing a game for the Merseysiders.
Rating per club: Arsenal 4/10, Liverpool 0/10
10. Jim Furnell
Furnell had made only two league appearances as a professional by the time he joined Liverpool from boyhood club Burnley in February 1962. The goalkeeper was immediately installed as first-choice glovesman at Anfield for the remainder of the campaign, helping the Reds back into the First Division under the management of Bill Shankly.
Furnell lost his place to Tommy Lawrence in the top flight, however, which led to him joining Arsenal in late 1963. The shot-stopper kept hold of the No.1 jersey for much longer in north London, but the mid-1960s was a difficult time for the Gunners, who didn’t finish higher than seventh in Furnell’s five years at the club.
Rating per club: Arsenal 6/10, Liverpool 4/10
9. Jimmy Carter
After making a name for himself at Millwall, Carter was signed by Kenny Dalglish for £800,000 in January 1991. The legendary Liverpool manager resigned soon after, though, leaving the winger looking for a way out just a few months after pitching up at Anfield. By the time of his departure for Arsenal, Carter had played only five league games for the Reds.
During his three-and-a-half seasons at Highbury, the wide man won the FA Cup and League Cup in 1993, before getting his hands on the Cup Winners’ Cup the following season. He was rarely a regular starter, however, making only 25 league appearances before joining Portsmouth in 1995.
Rating per club: Arsenal 4/10, Liverpool 1/10
8. Jermaine Pennant
Eyebrows were raised when Arsenal splashed £2m on a 15-year-old Pennant, who became the club’s youngest ever player when he made his debut aged 16 years and 319 days in November 1999. The winger spent seven seasons at Arsenal but made just five Premier League starts and scored a total of three goals, all of which came against Southampton in May 2003.
After a series of loans and a brief stint at Birmingham, Pennant joined Liverpool in 2006, featuring in 81 games for the Anfield club. The highlight of his career was playing the full 90 minutes of the 2007 Champions League final against Milan, although Liverpool fell to a 2-1 defeat in Athens.
Rating per club: Arsenal 2/10, Liverpool 5/10
7. Alex Oxlade-Chamblerlain
Oxlade-Chamberlain joined Arsenal from Southampton in 2011 and made 198 appearances during his time with the London club, notching 20 goals and winning three FA Cups. He made his debut in the infamous 8-2 defeat by Manchester United at Old Trafford and, four years later, scored the only goal to help the Gunners win the Community Shield ahead of Chelsea.
Keen to play in his preferred central midfield position rather than at right wing-back, Oxlade-Chamberlain joined Liverpool for £35m in August 2017. His initial displays suggested the Reds had made a mistake – the England international’s debut came in the 5-0 hammering by Manchester City – but the 24-year-old has improved of late and could prove to be an excellent signing.
Rating per club: Arsenal 7/10, Liverpool 6/10
6. Yossi Benayoun
Benayoun made his name in English football at West Ham, before moving to Liverpool in 2007. Almost certainly the only Israeli ever to bag hat-tricks against both Havant & Waterlooville and Besiktas, he also scored at the Bernabeu against Real Madrid and notched twice in a thrilling 4-4 draw with Arsenal in April 2009, which is best remembered for Andrey Arshavin’s remarkable four-goal haul.
Benayoun joined Chelsea in summer 2010, but a lack of game time led him to Arsenal a year later. He scored six goals during his single season with the Gunners, including in a 3-2 triumph over West Brom on the final day which helped Arsene Wenger’s men finish in third place and above rivals Tottenham.
Rating per club: Arsenal 6/10, Liverpool 7/10
5. Michael Thomas
Thomas will always be remembered for scoring that goal for Arsenal, a late strike against Liverpool at the end of the 1988/89 season to take the title away from the Reds and into the Gunners’ grasp. The midfielder, who came through the youth ranks at Highbury, helped the club win the League Cup (opponents in the final: Liverpool) in 1987/88 and made 163 First Division appearances in his seven years within the first-team ranks.
Thomas moved to Anfield in December 1991 after falling out with Arsenal boss George Graham. His debut season concluded with the two-time England international scoring the opening goal in the FA Cup final defeat of Sunderland, but injuries limited his game time and he eventually joined Graeme Souness’ Benfica in 1998.
Rating per club: Arsenal 8/10, Liverpool 5/10
4. Geoff Strong
Strong is the only player in history to move between Stanley United and Arsenal, but his debut for the latter was delayed by National Service following his transfer in 1957. He finally featured for the Gunners three years later, scoring in a 5-0 defeat of Newcastle, before going on to form a formidable strike partnership with Joe Baker – both forwards netted 31 times in 1963/64.
Strong, though, was frustrated at a lack of silverware and moved to Anfield in November 1964. The inside forward won the FA Cup just 16 appearances into his Liverpool career, while he went on to lift the league title after the Reds finished on top of the pile in 1965/66. By the time of his exit to Coventry in 1970, Strong had played 155 league games for the club.
Rating per club: Arsenal 7/10, Liverpool 7/10
3. Nicolas Anelka
Arsene Wenger paid Paris Saint-Germain £500,000 for the 17-year-old in 1997, the unheralded striker playing a minor role in his debut Arsenal season before winning the Premier League title and FA Cup the following year. The striker finished the 1998/99 campaign as his side’s top scorer, which persuaded Real Madrid to buy the Frenchman for £22.3m. Not a bad two-year profit for the Professor.
Having bounced back from the Bernabeu to PSG, Anelka returned to the Premier League on a short-term loan deal with Liverpool for the second half of 2001/02, scoring some crucial goals as Gerard Houllier’s side finished second in the league. The club opted against signing him on a permanent deal, however, preferring to buy El Hadji Diouf instead.
Rating per club: Arsenal 8/10, Liverpool 6/10
2. Kolo Toure
Arsenal signed the Ivorian centre-back from ASEC Mimosas in his homeland in 2002, with Toure going on to become a prominent member of the Invincibles side of 2003/04. The defender also won two FA Cups during his time in north London, making a total of 326 appearances for Arsene Wenger’s men before joining Manchester City in 2009.
Toure moved to Anfield on a free transfer in 2013 and was desperately close to winning a third Premier League title in his first season, but Liverpool fell just short as his former club City took the crown. After playing only 14 times in the Premier League in his final season with the Reds, Toure joined Celtic in 2016.
Rating per club: Arsenal 8/10, Liverpool 6/10
1. Ray Kennedy
Kennedy won every domestic honour available during his time at Arsenal and Liverpool, with a total of 18 trophies spanning 14 years at the two clubs.
Beginning his career as a centre-forward, Kennedy made his Arsenal debut in 1969 and went on to play a pivotal role as the capital club won the league in 1970/71, scoring the decisive goal against Tottenham on the final day which helped the Gunners leapfrog Leeds.
Liverpool spent a club-record fee of £200,000 on his signature in summer 1974, with Kennedy requiring just 22 minutes to score the first of his 72 goals for the club. Converted into a midfielder at Anfield, the Northumberland-born man played 393 matches for Liverpool in all competitions, winning five league titles and three European Cups.
Rating per club: Arsenal 7/10, Liverpool 9/10
Overall ratings: Arsenal 67, Liverpool 56
