Much of this is familiar territory for the Republic of Ireland. Defeat in Prague marks the country's sixth successive failed bid to reach the World Cup, while they are no strangers to penalty pain.
Their last shootout defeat came against Slovakia in the Euro 2020 play-off semi-final in Bratislava.
That was in an empty stadium, in stark contrast to the ear-splitting noise they had to contend with in Prague.
Hallgrimsson will be deeply frustrated given how his side troubled their hosts for much of the game.
Considering it was his goalscoring heroics that catapulted the Republic of Ireland to this stage, it was appropriate that Parrott struck the first blow.
And like he did for the first of his three goals against Hungary in Budapest, he kept his cool to score from the spot after referee Glenn Nyberg penalised Vladimir Darida's challenge on Nathan Collins following a pitchside monitor review.
Four minutes later, the Irish supporters who sang their hearts out all night greeted a second goal rapturously, but that was as good as it got as missed chances stacked up.
With Collins having hit the bar early on, Molumby cracked the woodwork with a wicked 53rd-minute effort and Parrott had a header tipped away by Kovar before Krejci struck to send the game to extra time.
After a lengthy delay following the injury to Szmodics, neither side found a winner before a dramatic penalty shootout that ended with yet more heartache for the Republic of Ireland.
Hallgrimsson must somehow lift his squad for a meaningless game against North Macedonia in Dublin on Tuesday before watching another World Cup tournament through gritted teeth.