PSV Eindhoven qualified for the Champions League knockout stage for the first time in nine attempts with a 1-1 draw against a nine-man Arsenal side who had Lauren and skipper Patrick Vieira dismissed on Wednesday.
PSV, who lost 1-0 at Arsenal in their Group E opener in September, took an eighth minute lead through defender Andre Ooijer but were pegged back by Thierry Henry's 31st minute equaliser.
Arsenal's poor disciplinary record then returned with a vengeance as Cameroon defender Lauren got a red card in the 65th minute and Vieira was sent off in the 78th, the 10th dismissal of the Frenchman's Arsenal career.
PSV failed to make their numerical superiority count, but the draw booked them into the last 16 courtesy of a 2-2 draw for Panathinaikos in their game at Rosenborg Trondheim.
The Dutch are top on top on 10 points, ahead of Arsenal (7pts), Panathinaikos (6pts) and Rosenborg (2pts).
The decisive final matches for the other qualifying slot from Group E will pitch Arsenal against Rosenborg at Highbury and Panathinaikos against PSV in Athens on December 7.
PSV, thrashed 4-0 at home by Arsenal four years ago, created the first danger after seven minutes when target man Gerald Sibon disturbed the Arsenal defence and Jefferson Farfan's shot was blocked.
Mark van Bommel took the resulting corner and Ooijer nodded home totally unmarked at the near post.
HENRY EQUALISES
Despite a nagging Achilles tendon problem, Henry came close to levelling after full back Wilfred Bouma failed to clear the ball in his own area, but the France international could only find the side netting.
However, he made no mistake minutes later, working a one-two with Fredrik Ljungberg and firing home a deft back-heel from the Sweden midfielder as he drifted in from the right flank, giving keeper Gomes no chance.
Arsenal's Spanish winger Jose Antonio Reyes came to life when he forced Gomes to stretch for his shot from just outside the box with six minutes of the second half gone.
A minute later, Robert Pires set up a chance for Sol Campbell, back after a lengthy injury absence, but the England defender came a toe-length short of putting the visitors ahead.
Arsenal looked in control, despite PSV skipper Van Bommel breaking through on the right flank, beating two defenders and having his shot blocked by keeper Jens Lehmann.
The game tilted PSV's way three minutes later, though, when Lauren collected his second yellow card for a bad challenge on Lee Young-Pyo.
Despite the disadvantage, Arsenal created the better chances to grab victory with Gomes denying Henry and Ljungberg.
After Alex wasted PSV's best chance of the second half from close range, Vieira was given his marching orders for a second bookable offence.
Vieira collected the 56th red card of manager Arsene Wenger's eight-year reign but their first since February, when former defender Martin Keown was dismissed in a League Cup defeat by Middlesbrough.
Lehmann prevented a late Dutch win with a fingertip save to a shot from Park Ji-sung, but the draw in Rosenborg meant PSV were still able to celebrate after the final whistle.
