Argyle bowed out of the Papa John’s Trophy despite beating Arsenal under-21s 5-4 on penalties following a 1-1 draw at Home Park.
Kieran Agard gave the Greens the lead midway through the first period, finishing off after great work from Jordon Garrick on the right.
But Arsenal hit back through England under-21 striker Flo Balogun just after halftime.
On a freezing cold evening, 1795 supporters watched on from the Lyndhurst Stand, only a five-goal swing for the Greens would do if they were to progress to the knockout stages of the competition for the first time since the format changed.
Ryan Lowe changed his entire starting eleven for the visit of the young Gunners, handing 17-year-old pro, Will Jenkins-Davies his first senior start.
With the game taking place a week from Remembrance Day, both sets of players, staff and supporters fell silent for poignant moment of reflection ahead of kick off.
It was a fast start for the Greens, with Jordon Garrick quickly testing the pace of his full back.
It was in his second foray forward that he managed to pick out Ryan Law, who had made his way into the box, but the left-wing back’s shot came back on teammate Shirley enabling Arsenal to clear. More on Garrick later.
Argyle continued to press and pinched the ball on the halfway line. It was Agard who won it and as he looked up on the halfway line, he spotted Okonkwo off his line but slightly over hit his effort and it drifted over the bar.
Arsenal had won their previous game 4-2, away to Leeds United in the Premier League 2, so keeping them out was going to be a tough task.
And no sooner had the Pilgrims had their chances, the Gunners made their first move. A deep cross from the left hand side found the blonde head of Mika Biereth, whose looping header beat Callum Burton and bounced off the crossbar.
They kept coming, a lovely passing move along the back suddenly sprung to life and Burton had to be at his best to deny Alebiosu who broke the Argyle back line.
The Greens best chance of the half came fifteen minutes in, Mayor drove through the middle of midfield, has options to his left and right, went right to Jenkins-Davies.
His eyes lit up, was this the moment for him to grab his first Argyle goal…Zak Swanson didn’t think so and slid in to hook the ball away.
The Pilgrims were growing into the game and the pressure finally told, 24 minutes into the game Garrick again, showed his full back a clean pair of heels and picked out Agard in the middle who finished calmly first time.
A striker of his experience was never going to miss that.
Arsenal started the second half with the bit between their teeth, they penned Argyle back and got their reward.
Flo Balogun, who had looked the most likely in a red shirt, got behind Tomlinson, rounded Burton and slotted the visitor’s level.
The Arsenal strike took the sting out of the game and it appeared to be meandering to a stalemate.
The only real chance of note in the second half came 12 minutes from time when the skipper for the night, Macaulay Gillesphey, let fly from range only to see his effort palmed away.
After a couple of saves from Burton to keep a late Arsenal onslaught out the game went straight to penalties.
After four spot kicks scored from the opening five penalties it went to sudden death, Burton saved from Oyalinka to give Shirley the chance to win it, he did and the Greens got the extra point.
This competition has been a tough one for Argyle in recent times and this year has gone the way of others before it.
But it’s not without its success, six Argyle debuts have been handed out this season with the latest of those being Caleb Roberts.
The sixteen-year-old joined Freddie Issaka, Will Jenkins-Davies, Carlo Garside, Oscar Massey and Angel Waruih in being handed valuable game experience.
Argyle (3-5-2): 25 Callum Burton (gk); 41 Ollie Tomlinson, 3 Macaulay Gillesphey (capt), 37 Brandon Pursall; 14 Jordon Garrick (36 Craske 65’), 44 Will Jenkins-Davies, 4 Jordan Houghton (39 Garside 45’), 10 Danny Mayor (49 Roberts 56’), 27 Ryan Law; 18 Kieran Agard, 42 Rhys Shirley. Substitutes: 46 Zak Baker, 36 Finley Craske, 39 Carlo Garside, 43 Oscar Halls, 45 Angel Waruih, 48 Freddie Issaka, 49 Caleb Roberts.
Booked: Garside 71’
Arsenal under-21s: 33 Arthur Okonkwo (gk); 26 Flo Balogun, 36 Tim Akinola, 37 Ryan Alebiosu (Foran 51’), 56 Joel Lopez (51 Ideho 88’), 58 Mika Biereth, 63 James Olayinka, 66 Omar Rekik (74 Walters 74’) , 69 Zak Swanson, 70 Kido Taylor-Hart, 86 Brooke Norton-Cuffy. Substitutes: 47 Ovie Ejeheri (gk), 41 Nathan Butler-Oyadeji, 51 Joel Idaho, 74 Reuell Walters, 75 Zach Awe, 77 Khayon Edwards, 79 Taylor Foran, 80 Jack Henry-Francis.
Booked: Rekik 64’
Referee: Will Finnie