49ers coach Kyle Shanahan coaches against his old boss on Thursday

SANTA CLARA - When Kyle Shanahan was looking to get into the NFL as an assistant coach more than a decade ago, his father, Mike, called Jon Gruden and asked him to hire his son for an entry-level job in Tampa.

Shanahan joined the Buccaneers as a quality control coach in 2004 on Gruden's staff and got his introduction to pro football on a staff that featured five assistants who have gone on to get head coaching jobs in the NFL.

“It was such a good place for me to go to because Jon was doing everything,” Shanahan said. “It wasn't just his stuff. He was always on top of it with the film, which everyone is now because of the computers and everything, but he was one of the first guys doing that stuff, probably being a little bit younger than most guys at that time and just introduced me to pretty much every play known to man.”

Now 14 years later, Shanahan gets his first chance to coach against his old boss when the San Francisco 49ers (1-7) host Gruden and the Oakland Raiders (1-6) on Thursday night.

Gruden said he took great pride in that staff that featured Mike Tomlin, Rod Marinelli, Jay Gruden and Raheem Morris during Shanahan's two seasons there in 2004-05. The Bucs won just five games the first season before winning the NFC South with an 11-5 record in 2005.

“We had a lot of fun back in those days. The woodshed, I called it,” Gruden said. “People are going to take me to the woodshed here pretty soon, if we don't get this thing going.”

Both the Raiders and 49ers are struggling heading into this matchup, with Oakland losing three straight and San Francisco on a six-game skid.

Shanahan has struggled without starting quarterback Jimmy Garoppolo, while Gruden's return to the NFL has been rocky after nine seasons as a broadcaster at ESPN.

But Shanahan believes Gruden will turn the Raiders around if given time and sees no signs that the game has passed him by.

“Jon lives and dies football,” Shanahan said. “He never got away from it. He probably had even more time to sit and look at everything, and not get so caught up in his own team. The whole league's evolved since then. It evolves year to year. But, you watch his system, he has a foundation of what he used to do and things like that, but he's kept up with everything.”