Josh Keeley was the man of the hour as Leyton Orient staged one of the biggest shocks of the Emirates FA Cup third round after dispatching Derby County on penalties.
Charlie Kelman opened the scoring for Leyton Orient after 20 minutes, pouncing on a failed Rams clearance to fire past Jacob Widell Zetterström.
But the O's would not be in the ascendancy for long, with Derby County restoring parity five minutes later when Marcus Harness squared the ball for Dajaune Brown to tap home.
Neither side could find a breakthrough in extra-time, with Leyton Orient reduced to ten men after Sean Clare was sent off for a second bookable offence.
And though it came down to the lottery of a penalty shootout, it would be the O's celebrating at the final whistle as they progressed to the next stage 6-5 on penalties after Keeley kept out Callum Elder.
OBIERO SENDS ORIENT THROUGH 🔴@leytonorientfc have upset the odds to beat Derby County on penalties!
— Emirates FA Cup (@EmiratesFACup) January 14, 2025
They'll face @ManCity in the next round 🏆#EmiratesFACup pic.twitter.com/XyYO6VqzuM
Over at Deepdale, a Milutin Osmajić double saw Championship side Preston North End battle to a 2-1 victory against League One outfit Charlton Athletic.
Osmajić put Preston out in front when he intercepted Alex Mitchell's short pass to Addicks shot-stopper Will Mannion and coolly slotted the ball into the net just after the half-hour mark.
Charlton drew level ten minutes later through Luke Berry, with Thierry Small finding the midfielder in space after skilfully ghosting past Duane Holmes as the sides entered the interval at 1-1.
The second half began with Osmajić restoring Preston's lead when he arrived to meet Ben Whiteman's corner, the Montenegrin's first-time finish rustling into the bottom corner of the net.
Undeterred, Charlton fought back, with Chuks Aneke's header forcing Freddie Woodman into a fine save as time ran out.
But Preston held on to book their ticket to the next round, where they will meet Wycombe Wanderers.
Elsewhere, two goals inside nine minutes from Thelo Aasgaard led Wigan Athletic to victory against fellow League One side Mansfield Town at Field Mill.
Aasgaard broke the deadlock when he latched onto Jonny Smith's cross to head home on 49 minutes, before doubling his tally with a sublime effort beyond the reach of Christy Pym.
Thelo Aasgaard just has a knack for scoring screamers.@LaticsOfficial#EmiratesFACup pic.twitter.com/nTaHk896pi
— Emirates FA Cup (@EmiratesFACup) January 14, 2025
Hosts Manfield Town enjoyed the better of proceedings in the first half, with Matthew Craig and Stephen McLaughlin firing at goal, though Latics shot-stopper Sam Tickle comfortably dealt with both efforts.
That seemed to awaken the visitors, with Tickle's upward punt met moments later by Smith, who could only watch as his effort clipped the outside of the post as the sides entered the break level.
After the restart, Aasgaard opened the scoring with a header into the roof of the net before securing his brace when he curled the ball home from the edge of the area to secure Wigan's place in the next stage of the competition.
The Latics will now host Premier League side Fulham in the fourth round.