Giancarlo Stanton appeared to tie the game when he pinch-hit for a grand slam in the bottom of the eighth inning Saturday.
But his hit to center field hit near the top of the fence for a three-run double that left the Yankees trailing by one and ending their 6-5 loss to the Cardinals at Yankee Stadium.
In the bottom of the ninth, Juan Soto doubled with two outs to make the game more interesting, and Aaron Judge was intentionally walked, bringing Austin Wells to bat with momentum on his side.
Wells hit a foul ball down the right field line and then struck out on a 3-2 slider to end the game.
The Yankees fell behind by five runs early in the game behind another poor performance from Will Warren, who likely won't start for the team this season, but Clark Schmidt and Luis Gil are close to returning from injuries.
And when the game really matters, Trent Grisham won't be under center, as he was on partial rest Saturday with Judge playing as the designated hitter.
September rolls around on Sunday and the next test begins in the Bronx as the Yankees try to hold off the Orioles and win the American League East.
And yet, while the Yankees have overcome similar problems many times before, Judge and Soto couldn't save the team.
Soto is just three hits in 22 at-bats over his last five games. Judge has gone five straight games without a home run for the first time in three weeks. His longest home run drought this season is eight games.
The seven innings of relief from St. Louis right-hander Kyle Gibson was somewhat unexpected, as Gibson had allowed 15 earned runs in 14 1/3 innings over his previous three starts.
But left-hander Matthew Liberatore allowed four consecutive hits with two outs in the eighth inning.
The Yankees loaded the bases against Liberatore and then singled by Judge, Wells and Jazz Chisholm Jr. before Anthony Volpe dribbled for four straight hits and Judge homered to make it 6-2.
Stanton pinch-hit for Grisham, with right-hander Andrew Kittridge coming up to bat for St. Louis.
Stanton hit a first-pitch slider 417 feet to center field to make the score 6-5.
Ben Rice replaced Stanton with a runner on base, but Alex Verdugo grounded out to end the inning.
In the ninth inning, Oswaldo Cabrera pitched to a full count against Ryan Helsley, but was fouled out for a pitch clock violation and struck out as the leadoff batter of the inning.
Gleyber Torres flied out, putting Soto and Judge on base, but Wells ended it.
The Yankees started well Saturday. Wells continued his strong performance at the plate with a leadoff double in the bottom of the second inning and scored on Volpe's single to left.
Warren continued pitching despite allowing walks in the first two innings, but things got tough in the third inning when he walked leadoff batter Victor Scott.
With a runner on first and one out, Nolan Arenado hit a timely single to center field to tie the game.
Brendan Donovan then hit a three-run homer to right field to put the Yankees up 1-4.
According to Baseballsavant.com, the ball was hit 334 feet to the right and would have been a home run in just one ballpark.
It marked just the fourth time Warren has allowed at least four runs in five MLB starts.
And it could have been even worse for Warren in the fourth inning, when Verdugo ended the inning by getting Paul Goldschmidt out at home plate on an Ivan Herrera single to left.
The Yankees had chances to come back in the fourth and fifth innings.
In the fourth inning, with a runner on second and one out, Volpe grounded out and Grisham swung and missed on a questionable check swing call.
Then they wasted a leadoff double by Verdugo in the fifth inning.
Mark Leiter Jr. has been as ineffective as ever since being acquired in a trade from the Cubs, and he made things even worse in the sixth inning.
Back-to-back doubles by Lars Nootbaar and Ivan Herrera brought in a run, and then Herrera scored on a wild pitch by Reiter and a throwing error by Wells to make it 6-1.
