Now, he'll find out what it's like to pitch under the roof of Tokyo Dome when he takes the ball on Sunday against the Yomiuri Giants, the team with a history richer than any other in Japan.
After edging the Hanshin Tigers, 6-5, on Saturday, Wakefield and the Red Sox will play one more exhibition game before opening the regular season on Tuesday against the Oakland Athletics.
The exhibition against Yomiuri is slated for 6:05 a.m. ET and can be seen live on MLB.TV.
"I'm looking forward to playing in a different country and getting a chance to compete against other people in Japan," said Wakefield. "I'm looking forward to being able to represent Major League Baseball internationally and to create opportunities for us to take our sport to a different level."
Wakefield won't be the only attraction for the fans. Sox reliever Hideki Okajima spent most of his Nippon Professional Baseball career pitching for the Giants (1995-2005), who play their home games at Tokyo Dome.
Okajima, who didn't pitch Saturday against Hanshin, is all but certain to pitch against his former team.
"What Oki did for us last year, starting out, kind of going under the radar, being an All-Star, helping us get where we wanted, I think we're all excited," said Red Sox manager Terry Francona. "All his teammates are pretty excited to see how he's received back here."
In downing the Tigers on Saturday, the Red Sox got a big taste of the atmosphere of the Japanese fans.
"It was definitely an experience," said Sox first baseman Kevin Youkilis. "It was a lot of fun to go out there and it was something different. It was a lot of fun. It was a fun game. The fans got into it. They were very respectful of the game and they know the game very well. It's great to get away from Fenway Park and play in a great stadium like this."
Following the game against Yomiuri, the Red Sox will have the day off on Monday. They will then open their season against the Oakland Athletics in Tokyo at 6:05 a.m. ET on Tuesday. The teams will play one more game on Wednesday.
Ian Browne is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.