Goalkeeper Bentley saved two penalties in a nerve-jangling shoot-out against Wycombe as the Shrimpers secured a return to League One.
They did it the hard way, though, having blown their chance of automatic promotion, with a shock final-day defeat at Morecambe condemning Southend to the play-offs.
But Bentley, 21, smiled: “It was in our hands on the last day of the season but we didn’t want to go up automatically.
“We fancied Wembley and coming up this way instead. Thankfully it went our way and I’m just ecstatic for the lads and for the club. It’s fantastic.”
It looked as though it was not going to be Bentley’s day when he was credited with an own goal after Joe Jacobson’s free-kick bounced down off the crossbar and deflected in off his back five minutes into extra-time.
But substitute Joe Pigott got Southend out of jail with an equaliser in stoppage time to make it 1-1 and Bentley grabbed his second chance, keeping out penalties from Matt Bloomfield and Sam Wood to secure a 7-6 shoot-out success.
For manager Phil Brown it was a second play-off triumph, having famously guided Hull into the Premier League seven years earlier.
The 55-year-old has slipped down the leagues since those heady days but still fancies another crack at the top flight.
“I don’t want to be in the second division all my life. I’ve got ambitions and I want to be back in the Premier League if I can,” he said.
“I’m a lucky man, I’ve managed four different clubs. A lot of young talent out there only gets one chance. It’s a brutal game.”
For Wycombe, another season in the basement division beckons, but boss Gareth Ainsworth insists they were punching above their weight this term.
“We have a five-year plan and this was only year one,” he said.
“The plan this year was 55 points and survival. We are ahead of the plan, the play-offs were supposed to be year three – I’ve gone off like a train!”