Can Raiders, Jon Gruden recapture magic of 1999 finale at Arrowhead Stadium?

Woodson, Bruschi: Chiefs will get home win vs. Raiders (0:44)

Darren Woodson and Tedy Bruschi agree that the Chiefs will close the regular season with a home win vs. the Raiders. (0:44)

ALAMEDA, Calif. -- Al Davis had a certain glint in his eye when Jon Gruden's name came up that day in October 2008.

Sure, the news conference was all about Davis' firing of Lane Kiffin and elevating Tom Cable as interim head coach of the Oakland Raiders, but Gruden's name was uttered, same as it ever was.

"Jon was a good coach," Davis acknowledged nearly seven years after trading Gruden to the Tampa Bay Buccaneers for two first-round draft picks, a pair of second-rounders and $8 million.

"But don't forget, I took Jon [when] no one else even knew who he was. Jon's first two years, he was in tough. He won a big game that kept him alive. You know which game that was?"

Yeah, history -- with a few tweaks, of course -- has a funny way of repeating itself as the Raiders visit the Kansas City Chiefs on Sunday.

It was in the regular-season finale against the Chiefs in 1999, the end of Gruden's second season, that the then-wunderkind coach was on the famously impetuous Davis' chopping block. And why not?

After starting his rookie season of 1998 with a 7-3 record, Gruden's Raiders faded late to finish 8-8, no matter that Oakland had doubled its win total of the season before. In 1999, with a new quarterback in Rich Gannon still learning his system (sound familiar, Derek Carr fans?), Gruden's Raiders were filled with fits and starts, never winning more than two in a row and never losing consecutive games, either.

Indeed, Gruden, then a tender 36 years of age, headed to Kansas City with the Raiders just 7-8 and his job on the line.

Gruden in 2018 -- courtesy of the 10-year contract bestowed upon him by the late Davis' son, Mark, in January -- is not coaching for his job on Sunday at Arrowhead Stadium. Not with the younger Davis telling ESPN.com in November, "Having Jon Gruden here was the endgame for me. Jon's going to be the stability here. Jon's going nowhere. That's just the way it is."

But there are similarities.

The 2018 Raiders, as they were in 1999, are playing for pride in Week 17, having gone 3-3 after a 1-8 start and Davis' vote of confidence for Gruden. The Raiders can play spoiler against the Chiefs, just as they did in '99.

"We're playing good football in December, and we have one opportunity left, and it's against the team that we hate the most, right, guys?" Gruden told the Raiders in their victorious locker room after they beat the Denver Broncos on national television on Christmas Eve.

"They don't like us, either, so it's going to be a lot of fun."

As much fun as Gruden and the Raiders had on Jan. 2, 2000?

After trailing the Chiefs 17-0 in the first quarter of that game -- Kansas City led 14-0 before its offense touched the ball, courtesy of a Tamarick Vanover 84-yard punt return for a touchdown and a James Hasty 34-yard pick-six -- it seemed that Gruden would be joining Mike White and Joe Bugel as short-time Raiders coaches.

Then Marquis Walker blocked Daniel Pope's punt, and Kenny Shedd picked up the football and returned it 20 yards for an Oakland touchdown. And then Gannon warmed up, hitting Zack Crockett, Napoleon Kaufman and Tyrone Wheatley for touchdowns as the Raiders stormed back for a 28-24 halftime lead.

The dramatic "Wheatley won't go down" 26-yard touchdown run on which the Raiders running back seemingly bounced off all 11 Chiefs defensive players put the Raiders up 35-31 late in the third quarter.

Still, the Raiders had to rally late to force overtime. Gannon's 20-yard completion to Tim Brown on fourth-and-12 was a key play before Joe Nedney's 38-yard field goal tied the score 38-38 with 50 seconds to play ... all before Pete Stoyanovich missed a 44-yard field goal attempt as time expired.

The Chiefs did not touch the ball again. The Raiders got the ball first in overtime and drove to the Kansas City 15-yard line. Then Nedney drilled the game-winning (rules at the time had the first team to score in OT the victor) 33-yard field goal after 4 hours, 47 minutes of white-knuckle football.

Not only did Gruden save his job by giving the Raiders their first win at Arrowhead Stadium since 1988, but Oakland also denied the Chiefs the AFC West title and knocked them out of the playoffs.

The 2018 Chiefs have already clinched a playoff berth, but the Raiders could knock them from the conference's No. 1 overall seed and force them to play on wild-card weekend.

"You just put the Kansas City Chiefs tape on [for our players]," Gruden said this week. "They realize that Kansas City is leading the division and has a chance to lock up home field. They've got a very talented football team, best record in [the AFC]."

Earlier this month, the Raiders fell to the Chiefs 40-33 after closing to within 33-30 with just more than six minutes to play.

"We also know that if we didn't turn the ball over three or four times the last time, we were right there with them in the fourth quarter," Gruden said.

After Gruden won that 1999 finale, the Raiders claimed consecutive AFC West titles. In 2000, they went 12-4, led the NFL in scoring with 479 points and hosted the conference title game. Then they jumped to a 10-3 start in 2001 before losing three straight to close, and they advanced to the divisional round after beating the New York Jets.

Then came the game against New England.

"The Tuck Game," Davis the Elder rued, "was the undoing of a lot of things."

It was the last game Gruden coached for the Raiders until this season.

What's that about all that is old is new again?

"I think we are excited to finish this season with as much authority as we can," Gruden said. "I'm really proud of the way our guys have been playing."