The Raiders saw that commanding half-time lead become a 21-17 deficit in the third quarter but Josh Jacobs ran in the winning touchdown – his second of the night – with less than two minutes remaining.
That meant it was third time lucky in London for the Raiders, twice beaten at Wembley but the first to celebrate in Tottenham.
Years of planning had gone into this game, with hosting such events so integral to the design of this stadium that pre-game announcements were calling it "the first purpose-built NFL stadium to be constructed outside the United States".
Tottenham supporters may have a few issues with that statement, but NFL fans in attendance had no complaints about the facilities.
The entertainment was pretty good too as the Raiders tore up the script in the first half to keep the Bears' vaunted defence under pressure – with a little help from Chicago's makeshift offence.
Harry Kane may have been thankful that the pitch on which Spurs were brushed aside by Bayern Munich in midweek had been removed, slid under the south stand on enormous trays which reveal the NFL-ready surface below, though he still heard boos as he conducted the pre-game coin toss.
Once that was over, the Raiders got to work scoring more points against the Bears in a single quarter than they had conceded in any game this season.
It began with the first play of the second quarter when Jacobs ran in a touchdown from 12 yards, and things soon got worse for Chicago.
On their next drive quarterback Chase Daniel, starting in place of the injured Mitch Trubisky, was intercepted by Nicholas Morrow, who ran the ball back to the 24-yard-line.
After DeAndre Washington ran the ball in from three yards they led 14-0, and Daniel Carson added a field goal before the break to give Oakland a 17-0 half-time lead.
Momentum immediately shifted at the start of the second half as a careless toss from Derek Carr missed Jacobs in the backfield and ex-Raider Khalil Mack powered through to pounce on the loose ball before David Montgomery ran in a touchdown a few plays later.
The Bears were not done there. Daniel hit Anthony Miller from 32 yards to put them in touching distance of the end zone and two plays later Robinson snared a nine-yard touchdown pass.
And they completed the turnaround before the third quarter was over. Tarik Cohen's 71-yard punt return electrified the stadium and put Chicago on Oakland's 16-yard line, from where Daniel found Robinson in the end zone as the Bears went 21-17 up.
Oakland looked poised to regain the lead at the start of the fourth as Trevor Davis ran to the end zone but Sherrick McManis stepped in to punch the ball out of his grasp on the goalline, and the Bears scooped up possession.
That set up a tense finale. Chicago thought it was in the bag when Erik Harris appeared to fumble the ball on his own 31-yard line and Buster Skrine hoovered it up, but the call was reversed after review and Oakland drove on.
Foster Moreau grabbed a 16-yard pass from Carr on the two-yard line and Jacobs ran in the score with one minute 57 seconds remaining in the game.
The Bears had one final drive to try and save it, but when Daniel was picked off by Gareon Conley with 74 seconds left, the game was effectively over.
The NFL will be back for more next Sunday, when the Carolina Panthers and Tampa Bay Buccaneers meet here.
The league has a commitment to stage at least two games here per year for the next decade – just the start of what Tottenham hope will be a sizeable return on their investment. The early signs are good.