Winn, who entered the contest batting .182 with no homers or RBIs, went 2-for-3 with a solo homer and two runs scored. The journeyman outfielder, who is a longshot to make the team, went yard off Pirates starter Kevin Correia in the fifth inning, a play that caused center fielder Andrew McCutchen to lose his glove. McCutchen nimbly hopped the fence to collect his mitt and was greeted with rousing applause.
Correia, making his fourth spring start, cruised through three scoreless innings before running into trouble in the middle of the game.
Nick Markakis -- who was thrown out trying to stretch a triple in his first at-bat -- sent a 3-0 pitch into right field for an RBI single and finished 3-for-3 on the day. The Orioles scored another run courtesy of Vladimir Guerrero's sacrifice fly, and Mark Reynolds added a two-out RBI to give the Orioles a 3-2 edge.
The 30-year-old Correia's final line was four runs on seven hits and a walk over five innings.
"The command was good," Correia said. "Everything was pretty good except one inning, when I kind of got a little quick to the plate trying to keep the running game down. I know that's something that I tend to do when guys get on base, so I need to work on it before the season starts."
Orioles starter Jake Arrieta exited after four innings of two-run baseball, scattering eight hits and striking out six. Arrieta, who has been working off his fastball, threw 49 of 67 pitches for strikes in his third spring start.
"I thought it was a really positive outing," Arrieta said. "A ton of strikes. I felt comfortable with all my pitches, my depth on the breaking ball was very good, same thing with the slider. My changeup is coming along. I don't think I could be happier with the progress up to this point."
Scott Olsen made his spring debut for the Bucs, allowing one run in one inning of work. Olsen came on in the eighth and got two out before surrendering a solo homer to Nick Green.
Joe Beimel, also making his spring debut, was tagged for three runs (one earned) in one inning.
Up next for the Pirates: Pittsburgh will enjoy its first of two off-days this spring on Tuesday before resuming Grapefruit League play on Wednesday. Paul Maholm will start Wednesday's 1:05 p.m. ET home game against the Blue Jays. Joel Hanrahan and Jeff Karstens are also expected to pitch for the Pirates, who are 1-2 against Toronto this spring.
Up next for the Orioles: The O's will welcome the Houston Astros for their third consecutive home game on Tuesday afternoon at 1:05 p.m. Baltimore will send Brad Bergesen to the hill, looking to rebound from his last spring start. Houston will counter with Aneury Rodriguez, who was a late addition given Wandy Rodriguez's injury. The contest will be broadcast on MLB Network and MASN.
Brittany Ghiroli is a reporter for MLB.com. Read her blog, Britt's Bird Watch, and follow her on Twitter @britt_ghiroli. This story was not subject to the approval of Major League Baseball or its clubs.