Arsenal were forced to settle with a draw in Lisbon as Sporting Lisbon held the Gunners to a 2-2 draw.
A goal from a corner from William Saliba was cancelled out by Goncalo Inacio's header from a corner moments later.
Just after the start of the second half, Sporting took the lead through Paulinho in a good move that left Arsenal stunned.
The Gunners got a goal back after Granit Xhaka's shot was deflected into the back of the net off Sporting midfielder Hidemasa Morita, which was registered as an own-goal.
It's all to play for at the Emirates, here are our player ratings from the opening leg in the Round of 16.
Matt Turner: 6 - Sloppy in areas but corrected his errors, could have done better for Sporting's opener.
Zinchenko: 7 - Everywhere as usual, played intricate passes through the lines to give the Gunners chances out of nothing.
Kiwior: 5 - Should have done better for Inacio's goal from the corner, an ok debut for a player that hasn't played with this side before.
Saliba: 7.5 - Confident, reliable and got a rare goal, a rounded performance by the Frenchman.
White: 6.5 - Confident on the ball, covered well considering the pace in Sporting's attack.
Xhaka: 7.5 - Popped up all over the pitch, a controlled performance from tonight's captain.
Jorginho: 6 - Won the ball back a few times in threatening areas in midfield, good passing ability as always.
Vieira: 7 - Encouraging play from the midfielder, had a few chances himself and looked positive every time he was on the ball.
Nelson: 7 - Always looking for the ball, made good runs and was direct in possession.
Martinelli: 7 - Lively on the ball, a great run in the second half that would've been a wonder goal from the Brazilian.
Saka: 6.5 - Not on the ball as much as normal but always direct and positive.
Subs:
Partey: 7 - Added control to the midfield.
Smith-Rowe: 5 - Didn't have much involvement.
Gabriel: 6 - Commanding at the back.
Tomiyasu: 6.5 - Direct on the flank.