Stevenage moved into the knockout stages of the Bristol Street Motors Trophy after a draw at home with Gillingham.
The point was all Boro needed but for a while passage looked in doubt after Josh Andrews put the Gills in front.
But Dan Kemp, a second-half substitute, equalised on 68 minutes and despite a good spell after the goal, it finished 1-1.
As per the rules, a penalty shoot-out was required to decide the destination of an extra point.
Nine of the 10 were scored, Tyreece Simpson's miss giving Gillingham that dubious honour.
Alex Revell had promised there would be a lot of changes from the draw with Reading, as well as a liberal sprinkling of youth players.
In the end there was one from the academy among the seven changes in total.
Only Nathan Thompson, Nick Freeman, Kane Smith and Harvey White kept their places in the starting line-up from Saturday with Ryan Doherty among those selected from the U18s.
The bench had another three of the Boro bairns - Alfie Thornett, Lennie Brown and Louie Henry - while Gillingham included four ex-Boro players and had Luca Ashby-Hammond in goal, brother of Taye.
The maths were simple as far as Boro were concerned - avoid defeat and they were through.
Gillingham needed to win by two goals and by half-time they had got one of them.
There was some talk of whether play should have been stopped for a head injury to Kane Smith but the goal came mere seconds later, a low strike by Andrews flying in at Ashby-Hammond's near post.
The Gills also had a header from Ethan Coleman that the keeper needed to gather but other than a few forays forward, they hadn't caused too many problems.
The thing was, neither had Stevenage.
Aaron Pressley had the best opportunity right on the stroke of half-time from Smith's pull-back.
That was hit straight and low after taking a touch, but it was stopped by the keeper.
Luca Ashby-Hammond also had to beat away a Thompson shot but that was after a pull-back towards Elliott List, the right ball to play, was woefully underhit.
Young Doherty was one bright spark, with a thumping tackle on Jonny Williams bringing a cheer from the Lamex crowd.
A return thump by the veteran midfielder was the youngster's 'welcome to senior football' moment.
But other than that there was little signs of Boro going on to win it, or even getting the draw they needed.
The visitors made two changes at the break but there was no change in the pattern of the game so Stevenage made a triple change.
Mind what opportunities were coming were at that point falling to Gillingham.
First Jack Nolan flashed a shot on the turn just wide of Ashby-Hammond's left-hand post and then Joseph Gbode did the same on the break.
Conor Masterson then missed a glorious opportunity, glancing a free header from a corner wide of the far post, a chance he really should have buried.
Three minutes later Boro made him and Gillingham pay.
Kemp, one of those Stevenage subs, got away down the right and after skipping across the edge of the area, he fired to the right of Ashby-Hammond.
The goal gave the home side a real boost and there were chances for Thompson, a header from a corner blocked, and White, a hit from the left side of the box pushed out by Ashby-Hammond.
White also had a corner from the right that almost went straight in, Ashby-Hammond scooping it out off the line.
Once that spell had fizzled out, aided by too many whistles and breaks in play, it was a case of seeing the game out and getting through.
Youngster Brown was introduced and he almost had a glorious moment after good work by Tyreece Simpson.
He cut inside but a defender was able to get in the way.
Bristol Street Motors Trophy match details
Stevenage (0) 1 Gillingham (1) 1
Gillingham win extra-point 5-4 on pens
Stevenage: T.Ashby-Hammond, N.Thompson, Freeman, Smith, Freestone, List (Brown 86), White, Pressley (Simpson 58), King, Young (Aboh 58), Doherty (Kemp 58).
Subs (not used): Bouzanis, Thornett, Henry.
Goals: Kemp 68
Booked: White 60, Revell (bench) 79, King 87
Gillingham: L.Ashby-Hammond, Hutton (Ehmer 46), Clark, Masterson, Coleman, Nolan, Andrews (Wyllie 46), Williams, Clarke, Ogie, Gbode (Sargent 86).
Subs (not used): Turner, Williams, Wakeling, Dieng.
Goals: Andrews 26
Booked:
Added time: 1+3
Referee: Scott Simpson (Stoke-on-Trent)
Attendance: 832 (including 147 from Gillingham)
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