Williams pen 64, Gregory 83, O'Brien 89
Ness 41, Ladapo 67
FOR a very long time, in the Docklands of the capital, it looked like Argyle had, for the second time this season in the Carabao Cup, got into a lead then fought, line astern, to protect it.
However, unlike a heroic performance at Bristol City in the first round, Argyle could not hold on this time. They did, though, show fantastic spirit and organisation against tough Championship opposition.
Jamie Ness's goal in the first half gave the Pilgrims a deserved a lead, and even when Shaun Williams leveled from the spot, Freddie Ladapo immediately restored Argyle's lead.
However, goals from Hail Mary substitutes Lee Gregory and Aiden O'Brien turned the tide in Millwall's favour, and it is they, not Argyle, who will be in Thursday's round three draw.
Derek Adams reacted to Saturday's 5-1 defeat against Peterborough by starting the two central defenders he ended the game with, meaning a first start of the season for captain Gary Sawyer, and a return for Ryan Edwards, whose goal against the Boro scarcely lived up to the definition of consolation so often wrongly tagged to goals that offer little succour.
Joe Riley also came back into the side, at right back, while Stuart O'Keefe made his first appearance since joining the club on loan last week. Ashley Smith-Brown was the only survivor of the back four that began against the Posh.
On the face of it Argyle lined up with five central midfield players, but Conor Grant and O'Keefe were asked to play the widest of the quintet, with Yann Songo'o playing a little deeper than colleague Jami ness and Antoni Sarcevic.Freddie Ladapo was asked to plough alone furrow up front.
The organisation worked a treat from the off. Argyle's shape was organised, but not rigid, and the hard work of the midfield restricted Millwall, the Championship side, mainly to crosses from deep that Matt Macey collected like a training session.
Argye created the best chance of the first half, on the quarter hour mark. Good hassling in the midfield won the ball back, and eventually Sawyer hit a diagonal ball towards Ladapo. Freddie obliged, nodding down towards Ness, who improvised a quick one-two with Sarcevic, and was only denied by a sprawling save.
The pattern of Millwall having possession but little impact continued, although there was a heart-in-mouth moment when captain Shaun Williams went over in the area under Sawyer's challenge, but the panic from anyone in green and white was probably due to being used to the penalties against us of late. In truth, although one has 'seen 'em given', as they say.
If this hassling, bustling, uber-organised performance had not caught the eye enough, on 40 minutes it had something to protect.
It is essential, one feels, to note the importance of Riley, O'Keefe and Songo'o in wrenching the ball away from Millwall in midfield, with the latter hitting a superb channel ball for Ladapo to chase. It was was not necessarily for Freddie to reach, but to challenge for, and as his sheer presence forced Byron Webster into giving away a corner, it was job done.
Conor Grant delivered a swinging left foot cross, Ryan Edwards helped it on, and Ness looped a header into the net, almost in slow motion. It was no less than Argyle deserved to this point, and the lead was easily seen through to half-time.
Millwall started the second half with renewed purpose, forcing a corner and creating easily their best chance so far, but when the ball fell to Williams he seemed caught betwen smashing it and placing it, and ended up hitting a shot with little purpose which Argyle blocked and - eventually - cleared.
Just after the hour mark, after Jed Wallace was introduced from the bench for Jem Karacan, the Lions pounced. Tom Elliott got around Edwards, who instinctively pulled him back by the shirt. Referee Darren England had an easy decision to award a penalty, which Williams took very well, beating Macey, who dived the right way.
The narrative, then, would be that the senior team, once level, would impart pressure, with momentum, and go on to win the game. Except no-one told that to Freddie Ladapo.
It was rather slack defending to allow Ladapo space between their exposed back-line and high midfield, but his touch, feint and power to get around the defenders was exceptional, and his finish, low and into the corner, as cool as you like.
Millwall brought on Lee Gregory, who scored a four-fer when these teams met in the EFL Trophy three seasons ago, as their response, and he was soon flicking on a cross to find Elliott at the back post, but the former Wimbledon man's touch let him down in a great area.
Aiden O'Brien was the latest first-teamer to be sent on, as manager Neil Harris hoped his players could keep their cool more, and soon afterwards Elliott again got on the end of a cross, but headed wide.
Ladapo gave way for Ryan Taylor with just under quarter of an hour remaining, with the sub tasked with carrying on Freddie's sterling work.
Argyle were just about to bring on Graham Carey for O'Keefe, indeed they opted not to so as to be on the ball from a Millwall attack. So, wouldn't you know, this was the moment to see almost the first lapse in shape, allowing Jiri Skalak far too much space to fire in a cross that Gregory powered in with a close range header.
Heartbreakingly, in the last minute of regular time, O'Brien showed up in the area at the perfect time to finish a left-wing cross. It was less of a shot into the goal, and more the ball hitting a player who had made a perfectly timed run. Either way, it was a lethal blow to what had been a valiant Argyle performance.
From the Docklands, to the Dockyard Derby. See you all in Portsmouth, mateys.
Millwall (4-4-2): 13 Ben Amos; 12 Mahlon Romeo, 17 Byron Webster, 25 Murray Wallace, 2 Conor McLaughlin (22 Aiden O'Brien 76); 11 Shane Ferguson, 21 Jem Karacan (7 Jed Wallace 63), 6 Shaun Williams (capt), 26 Jiri Skalak; 19 Tom Elliott, 10 Fred Onyedinma (9 Lee Gregory 67). Substitutes (not used): 1 Jordan Archer (gk), 5 Jake Cooper, 20 Steve Morison, 34 Harry Donovan.
Argyle (4-5-1): 1 Matt Macey; 2 Joe Riley, 5 Ryan Edwards, 3 Gary Sawyer (capt), 23 Ashley Smith-Brown; 13 Stuart O'Keefe (10 Graham Carey 84), 7 Antoni Sarcevic, 4 Yann Songo'o, 6 Jamie Ness, 15 Conor Grant (20 Gregg Wylde 90); 19 Freddie Ladapo (9 Ryan Taylor 77). Substitutes (not used): 8 David Fox, 16 Joel Grant, 21 Kyle Letheren (gk), 25 Scott Wootton.
Booked: Edwards 64, Ness 90.
Referee: Darren England.
Attendance: 3,645 (635 away).