When Lionel Messi and Inter Miami step into Chase Stadium on Saturday for an MLS playoff elimination game, Messi, the winningest player in modern soccer history, will be playing to avoid an extreme rarity: a trophyless season.

In 20 of his 21 previous professional seasons — and in all 20 uninterrupted by Covid-19 — Messi won at least one team trophy. In 14 of those 20 seasons, he won two or more.

But in 2025, he has none. And now, after losing Game 2 of a best-of-three playoff series, he is one loss away from the second empty season of his glittering career.

MLS Cup is the last piece of silverware available to him in 2025, and his team must win four straight games — Saturday’s first-round decider against Nashville SC, then the Eastern Conference semifinal and final, then the MLS Cup final — to lift it.

Without it, Messi’s three years in Miami would be the least successful three-year period of his career, solely from a team perspective. In every other three-season window, he has won at least four trophies for club and country combined; since signing with Inter Miami in July 2023, he has won “only” the 2023 Leagues Cup (Miami), 2024 Copa América (Argentina) and 2024 MLS Supporters’ Shield (Miami).

He has also never gone three straight years without a domestic league title. But that’s what he is on the brink of here. Individually, he has been phenomenal in MLS, and will soon claim his second consecutive Most Valuable Player award. But Inter Miami, the most expensive MLS team ever assembled, flopped in the first round of last year’s playoffs against Atlanta, and now, having lost 2-1 to Nashville this past Saturday, is facing another must-win match earlier than expected.

A loss Saturday, or in later rounds after the November international break, would leave Messi with his third trophyless club season. His first, at Barcelona in 2007-08, came when he was 20 years old. But that summer, he won Olympic gold with Argentina, an honor that technically sits on his 2007-08 ledger. The following season, he and Barça began a remarkable run of eight Liga titles in 11 years.

They also won six Spanish Super Cups, six Copa del Rey crowns and three UEFA Champions League titles during that 2008-2019 period. Counting UEFA Super Cups and FIFA Club World Cups, they lifted 29 trophies in those 11 years.

Their streak ended in 2019-20, Messi’s only prior season without any team silverware whatsoever. (He ultimately won the tournament originally known as the 2020 Copa América and scheduled for that summer; but it was postponed to 2021 because of Covid.) That season, the worst in Barcelona’s recent memory, led to the dismissal of not one but two head coaches, Ernesto Valverde and Quique Setién. It was paused for three months and resumed in empty stadiums. It ended with an infamous 8-2 loss in the Champions League quarterfinals against Bayern Munich.

Thus began a turbulent stretch for Messi at the club level. He left Barça a year later (after collecting one last trophy, the 2021 Copa del Rey). He won league titles in France, but he and PSG failed in knockout tournaments. In MLS, he joined a last-place team, and although Miami built the league’s most talented squad, its dominance has been hindered by league-imposed spending restrictions.

All the while, Messi continued to fill his trophy cabinet, because he began winning with Argentina. After a drought that spanned multiple decades and inflicted unimaginable pain, he and Argentina’s national team broke through at the 2021 Copa América, then won the 2022 Finalissima (the match pitting Copa América and European Championship winners against each other), the 2022 World Cup and the 2024 Copa América.

That second Copa América triumph pulled Messi ahead of former Barcelona teammate Dani Alves into first place on the list of most team trophies won by an individual player in modern soccer. It was Messi’s 44th. Last year’s Supporters’ Shield, awarded annually to the MLS team with the most regular-season points, was his 45th (this figure excludes the youth world championship he won with Argentina’s Under-20s but includes the 2005 Spanish Super Cup, which Messi is technically credited with even though he wasn’t in the squad for either of the two games).

But a year later, the preseason favorites stumbled intermittently throughout the regular season, and ultimately finished third in the Eastern Conference — though only one point behind the Shield-winning Philadelphia Union. In the Concacaf Champions Cup, they succumbed to the Vancouver Whitecaps, 5-1 on aggregate, in the semifinals. At the Club World Cup, they reached the round of 16 but got steamrolled by PSG. In the Leagues Cup, they were outplayed and beaten by Seattle in the final, 3-0. (And per new MLS participation rules, they did not enter the U.S. Open Cup.)

So they have only one more shot at a 2025 trophy. If they survive this Nashville scare, they’ll get the winner of Game 3 between the Columbus Crew and FC Cincinnati. If they win that one-off quarterfinal on the weekend of Nov. 21, they would most likely travel to Philadelphia to face the Union in the Eastern Conference final.

Every match from here on out will be single-elimination, do-or-die. Miami will be favored, but Nashville on Saturday reminded Messi and friends that nothing will be easy.

“We must now swallow the poison, save it and keep it inside all week long so we can release that in front of our fans next Saturday,” Miami head coach Javier Mascherano said after the Game 2 loss. “It is time for us to be more united than ever, because I have a lot of faith that we will turn it around next weekend.”