Jurgen Klopp masterminded a stunning 97-point season in the Premier League only to be pipped on the final day by a relentless Manchester City.
In many respects, it would feel cruel for such a phenomenal side to finish the campaign without a trophy.
But that is exactly what will happen if Mauricio Pochettino's Champions League shock troops can seal silverware for Tottenham at Liverpool's expense in Madrid.
Klopp must overcome Spurs, as well as a wretched individual record in major finals.
Here, we look at some memories the charismatic German will hope to banish on Saturday.
2012 DFB-Pokal final: Borussia Dortmund 5 Bayern Munich 2
Shinji Kagawa gave Dortmund an early lead, one that was restored by Mats Hummels' penalty after Bayern's Arjen Robben had converted a spot kick of his own. Robert Lewandowski then took centre-stage with a hat-trick as Klopp's Dortmund closed out a domestic double. It remains his last victory in a final.
2013 Champions League final: Borussia Dortmund 1 Bayern Munich 2
The Klassiker rivals reconvened for the following year's Champions League final at Wembley but Jupp Heynckes' Bayern now held the upper hand. Mario Mandzukic opened the scoring before Dortmund's Ilkay Gundogan converted a 68th-minute penalty. Franck Ribery's backheel was snaffled by Robben for the winner a minute from time and Bayern would go on to complete the treble.
2014 DFB-Pokal final: Borussia Dortmund 0 Bayern Munich 2 (aet)
Pep Guardiola and Klopp were first pitted against each other when the Catalan took the reins at Bayern from Heynckes for 2013-14 and duly cantered to Bundesliga glory. Dortmund ended up 19 points behind their rivals but the 2014 DFB-Pokal final was a tight and keenly contest affair – goalless after 90 minutes before Robben and Thomas Muller struck in extra time.
2015 DFB-Pokal final: Borussia Dortmund 1 Wolfsburg 3
Klopp's final season at Dortmund threatened to implode completely before a recovery after the turn of the year averted a feared relegation battle and sealed Europa League qualification. A dream farewell looked to be in prospect but they were outgunned in the Pokal by a Kevin De Bruyne-inspired Wolfsburg. Pierre-Emerick Aubameyang poached an early opener for BVB but Luiz Gustavo, De Bruyne and Bas Dost all struck in a 16-minute period where goalkeeper Mitchell Langerak did not cover himself in glory.
2016 EFL Cup final: Liverpool 1 Manchester City 1 (aet, 1-3 on penalties)
Picking up the pieces from the disappointing denouement of Brendan Rodgers' reign, Klopp galvanised Liverpool in the 2015-16 season and had an early shot at silverware. Philippe Coutinho forced extra time after fellow Brazil international Fernandinho opened the scoring for City. The shoot-out was all about an Argentinian, though, as Willy Caballero saved from Lucas Leiva, Coutinho and Adam Lallana – allowing Yaya Toure to dispatch the winning penalty.
2016 Europa League final: Liverpool 1 Sevilla 3
The Reds rebounded from that setback to plot a path to the Europa League final, thanks in part to an astonishing comeback against Klopp's old employers Dortmund. Daniel Sturridge dispatched an exquisite 35th-minute opener with the outside of his left boot, only for competition specialists Sevilla to turn the game on its head after the interval. Kevin Gameiro levelled from the restart and a roving Coke struck twice as Unai Emery's team won their third consecutive title.
2018 Champions League final: Liverpool 1 Real Madrid 3
The Liverpool side Klopp took to his next showpiece was a different beast altogether, operating entirely in line with his high-intensity tactical demands. However, the most valuable part of his ensemble, Mohamed Salah, was infamously injured in a first-half tussle with Sergio Ramos. Another member of Klopp's vaunted forward line, Sadio Mane, did find the target to equalise but it would be a game bookended by hideous Loris Karius errors and a Gareth Bale wondergoal.