Joaquin Correa's 72nd minute equaliser left Liverpool fans sick to the stomach, with the points shared in a 2-2 draw against Sevilla.
The Reds, despite having gone behind early, had the better of the majority of the game but were left rueing more defensive errors as they took just a point from their Champions League opener, with a missed penalty by Roberto Firmino proving costly.
Having let five in on Saturday against Manchester City, you'd have been forgiven for thinking that Liverpool may have been looking to keep things a little tighter early on.
Sevilla strike early
However, things worked out in the complete opposite way, with Sevilla taking an early lead at Anfield.
A lax challenge from Emre Can had allowed the Spanish side to keep their initial attack alive, and there was no excusing Dejan Lovren's mistake as he completely fluffed his lines looking to clear Escudero's cross - Wissam Ben Yedder on hand to tap in.
Reds fire back in dominant fashion
Liverpool immediately looked to strike back and there was no surprise in Sadio Mane being their main threat, testing Rico with a dangerous shot on target.
It was Roberto Firmino, though, that would level up on 21 minutes. Engineered by Alberto Moreno, who was enjoying an impressive half.
Firmino was presented with a tap-in by the Spaniard after an impressive one-two between Moreno and his captain Jordan Henderson, the Brazilian making no mistake to restore parity on Merseyside.
Back on level terms, Liverpool had a goal of the season contender go just a miss.
Excellent work from Mohamed Salah and Georginio Wijnaldum in their right defensive zone saw the Reds break with numerous men at a pulsating pace, the end-game seeing Emre Can shoot narrowly wide on his left after being played in by Firmino.
Sevilla, by that point, were firmly on the back-foot and it wasn't a surprise to anyone as the Reds took the lead.
Salah deserved immense credit as he won the ball back off the much more imposing Steven N'Zonzi on the edge of the area, but saw a slice of luck go his way as his resulting effort looped up off Simon Kjaer and into the net.
Costly missed penalty
Liverpool really should have been out of sight by half-time, nearly two ahead as Firmino missed a penalty.
Mane won it, with there being no argument from the Sevilla players as Pareja seemingly handled in the area, before then grappling and tripping the winger, the offences for which the penalty was finally given.
A shimmy and a shuffle accompanied Firmino's run up, but a goal didn't accompany his shot, which clanged off the post.
Still, Liverpool went into the break having completed a turnaround and things weren't getting much better for Sevilla as the referee sent off their manager in the opening exchanges of the second-half.
Eduardo Berizzo was understandably frustrated with the way his side had lost their lead, but gave the referee a simply decision by twice throwing the ball away from Liverpool players looking to take a throw.
The second time, an incident which sent Jurgen Klopp bonkers, Berizzo held the ball out to defender Joe Gomez, before turning away and throwing it.
Back on the pitch, Liverpool were seeking to continue their assault on Rico's goal, but were struggling to test him directly as both Firmino and Mane struck efforts off-target.
One man who did force the goalkeeper into a save was Georginio Wijnaldum, firing hard and low as a Henderson free-kick was headed away into his path, Rico equal to it as he pushed the ball away.
Reds rue missed chances
The hosts were made to rue their lack of a ruthless edge as the clock ticked past the 70th minute mark, Joaquin Correa taking the ball in his stride in the area, turning well before bending a finish past Loris Karius.
That equaliser proved the catalyst for Philippe Coutinho's re-introduction to the Liverpool match-day fold, replacing Can.
The Brazilian looked like he hadn't been away as he nearly made an impact from the off, a cute ball in Salah's direction just inches away from the winger as Rico gratefully grasped it.
Nearly a horror finish for hosts
Unfortunately, that would prove to nearly be the highlight of the final stages, with neither side mustering enough to fashion a good chance for a winner, until the final minute.
Sevilla were looking to lock in a point but found themselves one-on-one as substitute Luis Muriel shook off Gomez, firing wide of Karius' goal.
That error may have got to Gomez, who was sent off seconds later in the final act of the game for a late one.