Pedro Goncalves' strike from 46 yards was the furthest distance a player has scored from in the Europa League this seasonArsenal were knocked out of the Europa League at the last-16 stage in a penalty shootout defeat by Sporting Lisbon at Emirates Stadium.
Gabriel Martinelli's spot-kick was saved by goalkeeper Adan before Nuno Santos netted the winner to spark celebrations among Sporting's players at full-time following an eventful and entertaining tie.
A sensational long-range chip by Pedro Goncalves from 46 yards forced extra time after Arsenal's Granit Xhaka had earlier pounced on a rebound for the opener.
Arsenal defender Gabriel came agonisingly close twice in the final minutes of extra time when his header was tipped over the bar, and then he had an effort cleared off the goalline.
Sporting's Manuel Ugarte was also sent off after a dangerous sliding tackle on Bukayo Saka minutes before their shootout victory.
There were chances throughout in this frenetic second leg as Arsenal substitute Leandro Trossard hit the post in extra time when he was gifted possession and ran through one-on-one with the goalkeeper, only for Adan to touch it onto the woodwork.
Sporting forward Marcus Edwards, previously at Tottenham, was also denied by goalkeeper Aaron Ramsdale minutes after Goncalves made it 1-1 in normal time.
The visitors will find out their quarter-final opponents in Friday's draw (11:00 GMT).
Rotation fails to pay off for Arsenal
Despite the score being 2-2 on aggregate going into the match, Mikel Arteta made five changes to the Arsenal starting XI as he tried to make full use of his squad in the midst of a Premier League title race.
There was a welcome return for striker Gabriel Jesus, making a first start since December after recovering from a knee injury, but he could not convert before going off at half-time.
And Arteta was dealt an early blow when injuries to defenders William Saliba and Takehiro Tomiyasu forced him into first-half substitutions.
Sporting began well, controlling possession and creating numerous opportunities, despite Xhaka's powerful strike giving Arsenal a narrow lead.
They had a flurry of chances immediately after Goncalves' stunning equaliser too - Paulinho flicking a header over the bar and Edwards being denied by Ramsdale.
England goalkeeper Ramsdale had a busy evening, while Trossard, Martinelli and Gabriel all tested Adan at the other end.
Arsenal's European journey comes to an end but Arteta's concern will be the impact it could have on their Premier League campaign.
Injuries to key defenders and 120 minutes of gruelling action is not ideal preparation for their next league game against Crystal Palace in three days' time.
Freak goal catches out busy Ramsdale
Sporting reached the quarter-finals of a major European competition for the first time since 2017-18Arsenal goalkeeper Ramsdale was in the thick of the action but ultimately could not have a say in the penalty shootout.
Goncalves' audacious chip from just over the halfway line in normal time saw Ramsdale scrambling back to his goal in a helpless attempt to prevent it going in.
The equaliser stunned Arsenal and they were pinned back for minutes afterwards before Ramsdale responded with a superb save to deny Edwards when he raced through on goal.
As extra time kicked in, it felt inevitable Ramsdale would be called into action again in a shootout and he almost made his mark, getting his fingertips to Gonçalo Inacio's spot-kick, only to see it nestle inside the post as a wry smile crossed Ramsdale's face.
Defeat ends a run of six matches unbeaten in all competitions for Arsenal.
Player of the match
AdánAntonio Adán
Sporting Lisbon
Squad number1Player nameAdán
Squad number11Player nameNuno Santos
Squad number32Player nameTanlongo
Squad number33Player nameArthur Gomes
Squad number10Player nameEdwards
Squad number28Player namePote
Squad number26Player nameDiomande
Squad number25Player nameGonçalo Inácio
Squad number3Player nameSt. Juste
Squad number79Player nameYoussef Chermiti
Squad number84Player nameDário Essugo
Squad number2Player nameMatheus Reis
Squad number20Player namePaulinho
Squad number47Player nameRicardo Esgaio
Squad number17Player nameTrincão
Squad number15Player nameUgarte
Line-ups
Arsenal
Formation 4-3-3
1Ramsdale
18Tomiyasu12Saliba6Gabriel35Zinchenko
21Fábio Vieira20Jorginho34Xhaka
24Nelson9Gabriel Jesus11Martinelli
1Ramsdale18TomiyasuSubstituted forWhiteat 9'minutes12SalibaSubstituted forHoldingat 21'minutesBooked at 71mins6Gabriel35Zinchenko21Fábio VieiraBooked at 24minsSubstituted forØdegaardat 101'minutes20JorginhoSubstituted forParteyat 65'minutes34XhakaBooked at 45mins24NelsonSubstituted forSakaat 65'minutes9Gabriel JesusSubstituted forTrossardat 45'minutes11MartinelliSubstitutes
3Tierney4White5Partey7Saka8Ødegaard10Smith Rowe15Kiwior16Holding19Trossard30Turner56HillsonSporting
Formation 3-4-3
1Adán
3St. Juste26Diomande25Inácio
47de Sousa Esgaio15Ugarte28Pereira Gonçalves2Reis de Lima
10Edwards20Dias Fernandes17Machado Trincão
1Adán3St. Juste26DiomandeBooked at 118mins25Inácio47de Sousa Esgaio15UgarteBooked at 118mins28Pereira GonçalvesSubstituted forEssugoat 94'minutes2Reis de LimaSubstituted forGomes dos Santosat 94'minutes10EdwardsSubstituted forTanlongoat 119'minutes20Dias FernandesSubstituted forRamalho Chermitiat 90'minutes17Machado TrincãoSubstituted forGomes Lourençoat 105'minutesSubstitutes
6Alexandropoulos11Gomes dos Santos12Israel13Novo Neto16Costa Rocha18Fatawu32Tanlongo33Gomes Lourenço77Borges Cabral79Ramalho Chermiti82Espanha Fernandes84EssugoReferee:Antonio Miguel Mateu LahozLive Text
Match ends, Arsenal 1(3), Sporting Lisbon 1(5).
Penalty Shootout ends, Arsenal 1(3), Sporting Lisbon 1(5).
Goal! Arsenal 1(3), Sporting Lisbon 1(5). Nuno Santos (Sporting Lisbon) converts the penalty with a left footed shot to the top right corner.
Penalty saved! Gabriel Martinelli (Arsenal) fails to capitalise on this great opportunity, right footed shot saved in the centre of the goal.
Goal! Arsenal 1(3), Sporting Lisbon 1(4). Arthur Gomes (Sporting Lisbon) converts the penalty with a right footed shot to the bottom left corner.
Goal! Arsenal 1(3), Sporting Lisbon 1(3). Leandro Trossard (Arsenal) converts the penalty with a right footed shot to the bottom right corner.
Goal! Arsenal 1(2), Sporting Lisbon 1(3). Gonçalo Inácio (Sporting Lisbon) converts the penalty with a left footed shot to the bottom right corner.
Goal! Arsenal 1(2), Sporting Lisbon 1(2). Bukayo Saka (Arsenal) converts the penalty with a left footed shot to the bottom right corner.
Goal! Arsenal 1(1), Sporting Lisbon 1(2). Ricardo Esgaio (Sporting Lisbon) converts the penalty with a right footed shot to the bottom right corner.
Goal! Arsenal 1(1), Sporting Lisbon 1(1). Martin Ødegaard (Arsenal) converts the penalty with a left footed shot to the bottom left corner.
Goal! Arsenal 1, Sporting Lisbon 1(1). Jeremiah St. Juste (Sporting Lisbon) converts the penalty with a right footed shot to the top left corner.
Penalty Shootout begins Arsenal 1, Sporting Lisbon 1.
Second Half Extra Time ends, Arsenal 1, Sporting Lisbon 1.
Gabriel Martinelli (Arsenal) wins a free kick in the defensive half.
Foul by Dário Essugo (Sporting Lisbon).
Substitution, Sporting Lisbon. Mateo Tanlongo replaces Marcus Edwards.
Second yellow card to Manuel Ugarte (Sporting Lisbon) for a bad foul.
Ousmane Diomande (Sporting Lisbon) is shown the yellow card for a bad foul.
Martin Ødegaard (Arsenal) wins a free kick in the attacking half.
Foul by Ousmane Diomande (Sporting Lisbon).
