Reuniting in the EFL Cup third round 12 years after last crossing paths, Arsenal and Bolton Wanderers do battle at the Emirates Stadium on Wednesday evening.
The Gunners are out to end a trophyless streak in the competition that has lasted for over three decades, as not since the 1992-93 edition have Mikel Arteta's men come up trumps in the tournament.
However, two EFL Cup successes in 1987 and 1993 is still two more than the Trotters, who beat Mansfield Town on penalties in the first round before a 2-0 victory over Shrewsbury Town in their second game of the 2024-25 edition.
Here, Sports Mole takes an in-depth look at the head-to-head record and previous meetings between the two sides.
Head-to-head record
Previous meetings: 133
Arsenal wins: 58
Draws: 36
Bolton wins: 39
Formerly frequent foes during Bolton's lengthy stay in the top flight, Arsenal and Bolton Wanderers have crossed paths 133 times in all competitions, and the head-to-head history is actually closer than one may expect.
While Arsenal have prevailed in this fixture more times than their League One counterparts, the gap is not massive, as the Gunners boast 58 victories compared to 39 for Bolton, while there have also been 36 draws between the two clubs.
The most recent of those stalemates arrived in their last Premier League fixture in the 2011-12 season, where an Arsenal side helmed by current manager Arteta were held to a goalless draw away from home before Bolton slipped out of the top flight.
However, the Gunners' last win over the Trotters appropriately came in the EFL Cup that same season, as Andrey Arshavin and Park Chu-Young responded to a Fabrice Muamba opener in a 2-1 last-16 victory, a few months before the latter's distressing collapse at White Hart Lane.
Bolton do not have to go very far back for their most recent victory over the three-time Premier League champions, whom they defeated 2-1 in April 2011, a game where Daniel Sturridge opened the scoring before Tamir Cohen's 90th-minute winner.
That triumph represents the only victory that Bolton have managed in any of their last 14 clashes with Arsenal, though, and the Gunners had previously defeated the Trotters nine times on the bounce before that shock loss at what was once known as the Reebok Stadium.
Furthermore, Arsenal have never been beaten by Bolton at the Emirates, winning seven and drawing one of their eight clashes with the Trotters at their 60,000-seater headquarters, and their last home defeat to Wednesday's visitors came all the way back in a 1994 FA Cup fourth-round replay at Highbury.
As far as individual goalscorers are concerned, no player has scored more than Nat Lofthouse's 11 documented goals for Bolton in this fixture, while Doug Lishman leads the way for Arsenal with eight efforts against the Trotters.
Last 20 meetings
Feb 01, 2012: Bolton 0-0 Arsenal (Premier League)
Oct 25, 2011: Arsenal 2-1 Bolton (EFL Cup Last 16)
Sep 24, 2011: Arsenal 3-0 Bolton (Premier League)
Apr 24, 2011: Bolton 2-1 Arsenal (Premier League)
Sep 11, 2010: Arsenal 4-1 Bolton (Premier League)
Jan 20, 2010: Arsenal 4-2 Bolton (Premier League)
Jan 17, 2010: Bolton 0-2 Arsenal (Premier League)
Jan 10, 2009: Arsenal 1-0 Bolton (Premier League)
Sep 20, 2008: Bolton 1-3 Arsenal (Premier League)
Mar 29, 2008: Bolton 2-3 Arsenal (Premier League)
Oct 20, 2007: Arsenal 2-0 Bolton (Premier League)
Apr 14, 2007: Arsenal 2-1 Bolton (Premier League)
Feb 14, 2007: Bolton 1-3 Arsenal (FA Cup Fourth Round Replay)
Jan 28, 2007: Arsenal 1-1 Bolton (FA Cup Fourth Round)
Nov 25, 2006: Bolton 3-1 Arsenal (Premier League)
Feb 11, 2006: Arsenal 1-1 Bolton (Premier League)
Jan 28, 2006: Bolton 1-0 Arsenal (FA Cup Fourth Round)
Dec 03, 2005: Bolton 2-0 Arsenal (Premier League)
Mar 12, 2005: Bolton 0-1 Arsenal (FA Cup Quarter-Finals)
Jan 15, 2005: Bolton 1-0 Arsenal (Premier League)
Previous EFL Cup meetings
Oct 25, 2011: Arsenal 2-1 Bolton (EFL Cup Last 16)
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