The Raiders' 45-42 overtime win over the Cleveland Browns at the Oakland Coliseum on Sunday was Gruden's first win since Nov. 30, 2008, when he was with the Tampa Bay Buccaneers.
It is Gruden's first win with the Raiders since Oakland beat the New York Jets in a playoff game on Jan. 12, 2002.
As such, Gruden has tied Vince Lombardi in career coaching wins with 96 victories.
"It feels like my first win in a hundred years," Gruden said with a laugh. "It's just great to be back. I thank our fans for hanging in there with us. A lot of ups and downs. But to get that field goal with our third-string kicker, backup snapper, I've never been so nervous on a 29-yard field goal in my life."
Raiders owner Mark Davis was equally pleased to see his team back in the win column.
"I can smile again," Davis told ESPN. "It's been a long time."
Indeed, it was Oakland's first win since Dec. 3, 2017, when they beat theNew York Giants, and also ended a seven-game losing streak for the Raiders.
Rookie kicker Matt McCrane's 29-yard field goal with 1 minute, 46 seconds to play in the extra period improved the Raiders' record to 1-3 and dropped the Browns to 1-2-1. McCrane joined the team this week after an injury to Mike Nugent, whom Oakland had signed after Eddy Piñeiro suffered an injury in training camp.
McCrane redeemed himself after missing kicks from 47 and 50 yards out from the baseball dirt infield.
"My fiancé gets on me all the time for having no emotion," McCrane said. "But that's the life of a kicker. You take it one kick at a time and you move on and you reset, no matter what happened the previous kick. What a great win, though."
The Raiders, who had been outscored by a combined 64-17 in the second half in the first three games of the season and 37-3 in the fourth quarter, rallied late against the Browns, who held a 42-34 lead.
"We haven't fixed anything yet, you know we haven't fixed anything, we've got a lot of things we got to get better at," Gruden said of his team's growth. "I think it's pretty obvious ... but we have guys that are really eager to work, we've got good leadership, and we're going to continue to do it. But it was fun to score, and win a game, maybe get that monkey off our back."
Oakland forced overtime by driving 53 yards in six plays and 56 seconds, Derek Carr hitting tight end Jared Cook for his second TD of the day with 34 seconds to play. Carr then connected with Jordy Nelson for the 2-point conversion on a fade to the left corner of the end zone, beating former Raiders cornerback T.J. Carrie on the play.
Marshawn Lynch gave an impassioned speech to the offensive line in the first half and he finished with 130 yards rushing on 20 carries. It was his highest rushing total since he went for 140 yards for the Seattle Seahawks on Nov. 9, 2014, against the Giants.
Carr was picked off twice, giving him a league-leading seven interceptions, but he also had four TD passes to Nelson, Amari Cooper and Cook. Carr passed for 437 yards in completing 35 of 58 attempts.
Perhaps most rewarding for Gruden and the Raiders was beating former coach Hue Jackson, who had an 8-8 record for Oakland in 2011 but was fired by incoming general manager Reggie McKenzie.
Gruden and Jackson were on the same coaching staff at the University of the Pacific in 1989.
Raiders cornerback Gareon Conley had a 36-yard pick-six for the Raiders to give them a 7-0 lead about four hours before McCrane's field goal gave Gruden his first win in almost a decade.
McCrane hits game-winning FG in OT for Raiders
Matt McCrane drills a 29-yard field goal as the Raiders hold off the Browns in overtime 45-42.