Diego Simeone's quest for Champions League immortality fell short on Tuesday night, as Arsenal dashed Atletico Madrid's hopes of reaching a third European Cup final under the Argentine's leadership. The result means Simeone remains on the outside looking in at an elite club of managers who have guided the same team to three or more Champions League finals.

The list of those who have achieved this feat reads like a who's who of football royalty: Bob Paisley (Liverpool, 1977, 1978, 1981), Sir Alex Ferguson (Manchester United, 1999, 2008, 2009), Jürgen Klopp (Liverpool, 2018, 2019, 2022), Miguel Muñoz (Real Madrid, 1960, 1962, 1964, 1966), Carlo Ancelotti (Real Madrid, 2014, 2022, 2024), and Zinedine Zidane (Real Madrid, 2016, 2017, 2018). Notably, Real Madrid legends account for half of this exclusive group—a testament to the club's unparalleled European pedigree.

For Simeone, the opportunity to join that company was tantalizingly close. Atletico Madrid needed just a result at the Emirates Stadium in their semifinal second leg against Arsenal. But Mikel Arteta's Gunners had other plans, shutting the door on El Cholo's ambitions and keeping him stuck on two final appearances.

Those two finals remain painful memories for Atletico fans. In 2014, Los Rojiblancos were minutes away from lifting the trophy in Lisbon, leading 1-0 deep into stoppage time before Sergio Ramos rose to head home a 93rd-minute equalizer for Real Madrid. The game spiraled into extra time, and Atletico's dream dissolved in a 4-1 defeat. Two years later in Milan, history repeated itself in a different form—another final against Real Madrid, another heartbreak, this time decided on penalties.

For Simeone, the dream of a third final remains just out of reach. The list of three-time finalists stays intact, and for now, the Argentine will have to watch from the sidelines as the game's managerial greats continue to define Champions League history.