Teammate Grzegorz Krychowiak kickstarted the calamitous series of events by attempting to send a 60m back pass to his keeper on the hour mark.
Unbeknown to the Polish team, the fourth official decided this moment was the perfect time to allow Senegalese striker M'Baye Niang to re-enter the pitch after he had been momentarily sidelined to have a suspected injury checked on.
As Niang scurried towards the high-bouncing pass, Szczesny decided to come charging out to meet him but was beaten to the ball and was photographed looking hilariously out of position as Niang tapped home into an empty net.
It's the third major tournament in a row the Juve gloveman has begun in horrible fashion.
At Euro 2012 he conceded a penalty and was sent off after bringing down Greece's Dimitris Salpigidis in the opening match. After being handed a one-game suspension he never regained his place in the starting XI.
Four years later at Euro 2016, Szczesny was injured in Poland's opener against Northern Ireland and didn't feature again as his teammates made it to the quarterfinals.
It was supposed to be different this time in Poland's first appearance at a World Cup since 2006.
After being anointed as legendary Italian keeper Gianluigi Buffon's successor at Juventus, he became the fastest goalkeeper in club history to reach 10 clean sheets, hitting the mark in 14 games.
With a Serie A title under his belt he entered the World Cup brimming with confidence, even if he was rotated with former Arsenal teammate Lucas Fabianski in the lead-up friendlies.
But after getting the starting nod it's all gone pear-shaped again and you wonder if it will again be a case of one-game and it's all over with Fabianski waiting in the wings.
Krychowiak made some amends for his part in proceedings by scoring a late header but it wasn't enough as Poland joined fellow group favourite Colombia — which lost 2-1 to Japan — on the back foot.