PITTSBURGH -- Winless since June 17, Cardinals pitcher Adam Wainwright took the mound on Tuesday for a ninth time while looking for career victory No. 199. This time felt so different and so promising, he thought at the time and said later, especially considering the opponent and the way the game had progressed so nicely through four innings.

Then, as so often has been the case in a final MLB season that has been memorable for Wainwright only in the sense of its absolute awfulness, the veteran right-hander saw everything he had worked for -- and hoped for -- come crumbling down in a series of bad breaks and bad pitches. Everything Wainwright had done well while holding Pittsburgh to one run, one hit and one walk over the four innings was washed away by a potentially missed strike three call, an infield single, a bunt hit and rockets from Bryan Reynolds and long-time nemesis Andrew McCutchen.

The flurry -- one that resulted in the Cardinals losing 6-3 to the Pirates on Tuesday -- still baffled Wainwright more than 90 minutes later. How could such a strong start and his best chance to nab win No. 199 vanish so quickly?

“It’s proving to be very difficult,” the 41-year-old Wainwright said of trying to nab two more wins and get to 200 before he calls it a career. “I thought today was going to be the day, for sure. Especially after the way I started, I really felt confident that we were going to win that game. We just didn’t do it. I can’t win 200 before I win 199, and I’ve got to win that one first. And that starts with my next start. I’ve got to be focused on winning that game.”

The Cardinals lost for a sixth time in the past seven games, and they fell for a fifth straight time this season in Pittsburgh. The frustration boiled over late in the night when catcher Willson Contreras, manager Oliver Marmol and prized rookie Jordan Walker were all ejected by home plate umpire Brennan Miller. After years of beating up on their rebuilding NL Central rivals, the Cardinals are just 2-7 against the Pirates this season and 0-5 in Pittsburgh.

Nobody knows of that history better than Wainwright, who came into Tuesday 23-8 all-time against the Pirates and 11-4 at PNC Park. His 23 wins against Pittsburgh are the fourth most in franchise history and his .742 winning percentage against the Bucs before Tuesday was third best in MLB history.

Things looked even more promising for Wainwright when he got Pirates third baseman Vinny Capra to swing and miss in the third inning with an 82.1 mph cutter, per Statcast. Incredibly, Wainwright had a streak of 156 consecutive pitches that were not whiffs -- dating back to the third inning of Aug. 4 when Colorado’s Ezequiel Tovar whiffed in the third inning on an 86.8 mph sinker. Wainwright did not record a swing and miss in losses to the Royals or Mets, but he had some of his best stuff working on Tuesday.

The inability to consistently get swings and misses certainly shortens Wainwright’s margin for error, Cardinals manager Oliver Marmol said.

“He’s got to be a pitchmaker, which he was until he left some pitches over the plate, and they got hit,” Marmol said.

Capra started the fifth-inning rally that crushed Wainwright. Alfonso Rivas then recorded an infield single after Wainwright’s 1-2 pitch appeared to clip the strike zone. Following a bunt single and an RBI groundout, Reynolds crushed a ball off the wall for a double, and McCutchen went over the wall for the 299th home run of his career.      

“I either make really good pitches to him or really horrible pitches, and there’s no in between,” Wainwright said of McCutchen, who homered for a fourth time off the Cardinals' cornerstone. “He’s been a champion-type player for a long time, and it’s been an honor to battle against him.”

Said McCutchen of Wainwright: “I have nothing but respect for that guy. He's done it longer than I have. He's a competitor. He's going to compete every single time.”

Once 3-1 after beating the Mets in mid-June, Wainwright is now 3-9 with an unsightly 8.61 ERA. In many ways, his struggles mirror those of the Cardinals in their worst season in decades.

“It’s been a weird year, a funky year, and we haven’t had a year like this since I’ve been here,” Wainwright said. “So, if you have one of these every 18 years, that’s not a terrible ratio. I know with everyone it’s driving them crazy, and it’s driving me crazy. It’s not how I wanted to go out.”