After Andrew McCutchen singled and stole second, Milledge drove him in with two outs in the bottom of the ninth inning to give the Pirates a 4-3 victory over the Cincinnati Reds on Friday night after they blew a 3-0 lead in the late innings.
McCutchen singled through the hole at shortstop with two outs off Nick Masset (2-1), then stole second base on the first pitch to Milledge, making him 6-for-6 in steal attempts. Milledge worked the count full then grounded a single up the middle.
"Cutch definitely made the whole thing possible by stealing second base," Milledge said. "He's being very aggressive on the bases and he can really fly. The way he's going right now, it's hard to throw him out."
Added Reds manager Dusty Baker: "He's definitely the one guy you don't want on base in that situation."
Aware that Masset has 11 strikeouts in 6 2/3 innings, Milledge knew he was going to have to battle during his decisive at-bat.
"He's a good pitcher with really good stuff," Milledge said. "I just wanted to keep hanging in there until I eventually got something I'd be able to hit."
Octavio Dotel (1-0) got the win despite suffering his first blown save in three opportunities.
That came after the Reds parlayed five walks into two runs without the benefit of a hit in the seventh to cut the Pittsburgh lead to 3-2. Starter Zach Duke was lifted after walking Drew Stubbs on four pitches to begin the inning. With two outs, Javier Lopez walked Jay Bruce with the bases loaded to force in a run and Brendan Donnelly came on and forced home a second run by walking Ryan Hanigan.
Donnelly then escaped the jam by getting Paul Janish to foul out.
"Our bullpen struggled, but the big thing was that Dotel kept the game tied in the ninth and gave us a chance to win," Pittsburgh manager John Russell said.
Duke seemed on his way to raising his record to 3-0 before faltering in the eighth. He allowed one run and six hits in seven-plus innings with three walks and two strikeouts.
Reds starter Mike Leake worked seven innings in his second major league start, giving up three runs and seven hits with five walks and three strikeouts. Leake became the 21st player since the draft began in 1965 to make his professional debut in the major leagues last Sunday against the Chicago Cubs while not figuring in the decision.
Leake allowed all three runs in the first two innings.
"In the beginning, he was just throwing fastballs, but then he changed his game plan and went to more off-speed stuff," Baker said. "He really settled down."
Aki Iwamura singled to lead off the first inning and scored the game's first run when Leake made a throwing error on Milledge's sacrifice bunt. McCutchen, who also singled, came home on Garrett Jones' sacrifice fly. Iwamura's RBI single up the middle in the second made it 3-0.
Iwamura, McCutchen, Milledge and Ronny Cedeno each had two hits for Pittsburgh.
The start of the game was delayed 1 hour and 9 minutes by rain. ... Pittsburgh 3B Andy LaRoche left in the second inning with back spasms after drawing a walk and was replaced by Bobby Crosby. ... Pirates RHP Ross Ohlendorf (lower back spasms) has been scratched from his scheduled start Saturday night against the Reds and will likely be replaced by either LHP Brian Burres or RHP Daniel McCutchen, who would be recalled from Triple-A Indianapolis. Burres started in Ohlendorf's place Monday night at San Francisco. ... RHP Hayden Penn, who had been designated for assignment by the Pirates, cleared waivers and has until Monday to decide whether to accept an outright assignment to Indianapolis or become a free agent. ... Cincinnati manager Dusty Baker and pitching coach Bryan Price held a pregame meeting with RHP Aaron Harang, RHP Bronson Arroyo, RHP Johnny Cueto and RHP Homer Bailey, who combined to allow 22 runs in 20 1/3 innings in a four-game series split at Florida that ended Thursday night.