The Pirates will remember a very long night as one of the worst moments in their fast fade.
Ryan Ludwick drove in the winning run with a two-out infield single in the 14th inning, lifting the Cincinnati Reds to a marathon 4-3 victory Monday that handed the Pirates their fourth straight loss.
The Pirates' slump - 21 losses in the last 30 games overall - has dropped them a season-high 12 games behind the first-place Reds in the NL Central.
"Well, you know, I've heard that whatever doesn't kill you makes you stronger," manager Clint Hurdle said. "We're fighting through this thing. This has been a big push for us. It's been a hard time for a while."
Rick VandenHurk (0-1), who was called up before the game, started the 14th and gave up a single by Devin Mesoraco. Brandon Phillips reached when the Pirates failed to get a forceout on his grounder, and the runners advanced on a wild pitch.
Shortstop Chase d'Arnaud couldn't come up with Ludwick's grounder in the hole, finally ending it.
"I think we're pretty resilient," reliever Jared Hughes said. "It was just one of those games, unfortunately. We'll go nine innings, 14 innings, 19 innings, whatever it's got to be."
The Pirates loaded the bases with none out in the top of the 14th against Alfredo Simon (2-2) and failed to score - Jose Tabata grounded out to end the threat. The organist played "Take Me Out To The Ball Game" again between innings.
"Our offense had multiple opportunities to pick us up tonight, and it continues to not give us what we need when we need it," Hurdle said.
It was the Reds' longest game of the season in innings and time - 5 hours, 22 minutes. The Pirates played a 19-inning, 6-hour game against St. Louis last month.
Sam LeCure bailed out Reds closer Aroldis Chapman to keep it tied in the 10th, retiring Michael McKenry on a grounder with the bases loaded. LeCure struck out the side in the 11th.
Chapman had trouble getting his fastball up to speed in his first appearance since Friday, when he had his club-record streak of 27 straight saves snapped. Chapman walked the bases loaded around a pair of outs, his fastball topping out at 96 mph.
The Reds wasted a chance in the bottom of the 10th, leaving the bases loaded when Jay Bruce struck out. Bruce went 0 for 5, ending his nine-game hitting streak.
Plate umpire Phil Cuzzi warned both benches after Hughes hit Brandon Phillips in the leg with one out in the eighth. Phillips paused a moment, picked up the ball and tossed it back toward the mound before heading to first base. The Pirates were upset earlier in the season when a couple of their players got plunked in games.
"I was not expecting the ball to come back to me," Hughes said. "Usually the ball goes to the bat boy."
Hurdle wasn't upset by Phillips' gesture.
"It's kind of Brandon being Brandon," Hurdle said. "I don't have a problem with that."
The game drew 16,577 fans, the smallest crowd at Great American Ball Park this season. The second-smallest crowd of the season also was for a Pirates game - 16,859 for 5-4 Reds win on June 6.
Pittsburgh left-hander Wandy Rodriguez allowed only one hit through the first six innings - Chris Heisey's solo homer. Hughes relieved in the seventh and gave up a two-run double by Dioner Navarro that tied it at 3.
Andrew McCutchen homered off Mat Latos, who got a no-decision and remained unbeaten against the Pirates in his career. The right-hander gave up three runs and remained 4-0 in six career starts against Pittsburgh, allowing a total of nine runs.
NOTES: There were more than 500 dogs in the stands as part of a promotion that allowed fans to bring their pets. ... VandenHurk and d'Arnaud were called up before the game, along with RHP Bryan Morris. ... The Reds went 32-16 without 1B Joey Votto and are 2-3 since his return. Votto celebrated his 29th birthday. ... Reds SS Zack Cozart missed his sixth straight game with a strained oblique muscle. ... Reds 3B Scott Rolen took ground balls at third base before the game to test his back, which sidelined him for four games, and pinch-hit in the 13th. He grounded out.