Gabriel Martinelli missed from the spot as Arsenal crashed out of the Europa League after a penalty shootout loss to Sporting.
A 2-2 draw in Lisbon a week ago left this last-16 tie finely poised and it would go all the way at the Emirates Stadium, Sporting advancing 5-3 on penalties following a 1-1 draw after extra-time.
The visitors were perfect from 12 yards but Martinelli’s tame effort was saved in the first ever shoot-at the Emirates.
The reality for Arsenal is that all their hopes of a trophy this season now rest on their Premier League title charge, which continues at home to Crystal Palace on Sunday.
Granit Xhaka’s first goal since October had Arsenal ahead but they failed to build on that advantage before conceding a spectacular equaliser, reminiscent of the goal Nayim scored against the Gunners in the 1995 Cup Winners’ Cup final as Pedro Goncalves struck from over 49 yards out.
Substitute Leandro Trossard saw a shot turned onto the woodwork in the first half of extra-time before Manuel Ugarte was sent off, shown a second yellow for a lunge on Bukayo Saka.
The pressure ramped up in the shootout as the first seven takers all converted before Martinelli failed to do so, allowing Nuno Santos to smash home the decisive kick.
Earlier in the Europa League, Marcus Rashford fired Manchester United to victory at Real Betis with a rocket of a strike as Erik ten Hag’s side cruised through to the Europa League quarter-finals.
The Red Devils headed to Spain all-but assured of progress from this last-16 tie having won the first leg 4-1 in freezing conditions at Old Trafford last Thursday.
Betis made United sweat during the opening stages in the return fixture, but Rashford’s outstanding strike silenced the bouncing Estadio Benito Villamarin and secured a 1-0 win on the night.
The impressive 5-1 aggregate triumph puts them through to the quarter-finals, with Friday’s draw to outline their potential path to the Europa League final in Budapest.