O'Brien's astonishing ton took just 50 balls as the Irish recovered from 111-5 to beat Andrew Strauss' men and add to their wins in the 2007 World Cup over Pakistan and Bangladesh.
The result leaves England with a win, a loss and a tie from three dramatic games while Ireland's record World Cup run-chase means they have one win and one loss from their two matches so far.
England began their campaign eight days ago against the Netherlands in inauspicious fashion, securing a six-wicket win with just eight balls remaining.
A shambolic performance in the field featured overthrows, no balls for having too few fielders in the circle, and four dropped catches including sitters from Graeme Swann and James Anderson.
It all aided the Dutch on their way to making 292-6 with Essex batsmen Ryan ten Doeschate scoring 119 off 100 balls.
An opening century stand from Strauss and Kevin Pietersen in reply had seemed to ease nerves but, once the top order departed, the game was back in the balance until some lusty blows from Ravi Bopara.
Having struggled against the Netherlands, England fans feared the worst in the next game against the mighty Indian batting line-up.
It looked as if the pessimists might be correct as home favourite Sachin Tendulkar scored 120 off 115 balls to set India up for a big score.
But, from a position of 292-3 off 45 overs, India lost their last seven wickets for 33 runs to finish on 338 all out, thanks to the efforts of Tim Bresnan who took 5-48.
Bresnan's bowling ended up being vital as England, stirred by a magnificent 158 from skipper Strauss, put themselves in a position to make a record run-chase win the game.
At one stage, England required 61 runs for victory from nine overs but they then lost five wickets for the addition of just 26 runs in five overs.
The run rate had crept above more than two runs per ball and the pendulum had swung firmly in the Indians' favour.
India did not reckon on Bresnan contributing with bat as well as he had done with the ball, though, and he and Swann swished the bat to score 15 off the penultimate over.
But Bresnan was then bowled by Piyush Chawla and so the inexperienced Ajmal Shahzad had to face the final over.
Incredibly, Shahzad hit his first ball for a six to leave England needing five runs from three balls for victory which soon reduced to two runs from the last delivery.
Fearing an incredible defeat, India captain MS Dhoni set his field in such a way as to concede a single for a tied match.
England, aware that they also had done well to emerge from this game without defeat, took the run on offer gleefully in front of a stunned full house in the stadium.
The result seemed to leave England in good shape and in good spirits after the close call against the Netherlands.
But, astonishingly, England have proceeded to bowl and field as poorly in the match against Ireland as they had done in their opener against the Dutch - this time, to costly effect.
Having won the toss and elected to bat, England again made a decent score in excess of 300 with contributions from Ian Bell (81), Pietersen (59) and Strauss (34 on his 34th birthday).
The top score in the innings came from Jonathan Trott who hit 92 and, in doing so, became joint quickest man to reach 1000 ODI runs along with Sir Viv Richards and Pietersen.
However, with Trott as the last of the four main contributors departing in the 45th over, England stuttered over the line and their score of 327 should have been bigger.
It still looked more than enough, though, against an Irish team which had been bowled out for 178 by Bangladesh in their previous match.
That defeat in Dhaka had really hurt the Irish who appeared to have done the hard work by restricting the Tigers to 205.
But Ireland's run chase in Bangladesh faltered throughout and, once the O'Brien brothers, Kevin and Niall, were dismissed, they never looked like keeping enough men at the crease.
England also seemed to be exposing Ireland's batting line-up after skipper William Porterfield fell to a first-ball duck.
Paul Stirling, Ed Joyce and Niall O'Brien all managed to play themselves in but they made 32, 32 and 29 respectively and the required run-rate began to mount.
Once Gary Wilson was trapped lbw to Swann for just three runs off 14 balls, an England win seemed only a matter of time away.
What's more, the margin of victory would surely be even greater than the 48-run win in the 2007 World Cup.
However, those thoughts were soon evacuated once it was clear that Kevin O'Brien had decided to hit his way out of his side's seemingly desperate situation.
At first, there still seemed little to worry about. Surely, it was only a matter of time before he miscued a shot straight down the throat of a fielder.
But, aided by Alex Cusack, whose fine 47 from 58 balls has been understandably barely mentioned, O'Brien played the innings of his life.
Starting positively with a slog sweep off Swann for six in just his fourth over, O'Brien began as he meant to go on, scoring 13 fours and six sixes in an eventual score of 113.
Undoubtedly, he was also helped by another atrocious fielding performance from England who conceded yet more overthrows and dropped four catches in the innings as a whole.
Matt Prior and Strauss should be particularly embarrassed by notably botched efforts to dismiss Joyce and O'Brien.
And, despite the close shaves, O'Brien and Cusack scored at nearly 10 per over for almost 17 overs to push Ireland within sight of the finishing line.
It meant that, even when both had departed, the Irish - who, at one stage, had been 400-1 outsiders - were on the brink with only 12 runs required from 12 balls remaining.
Some fine hitting by Trent Johnson and O'Brien's other companion at the crease, John Mooney (34 not out off 30 balls), left Ireland needing three off the final over.
Mooney got them off Anderson's first ball to send Ireland back into dreamland in on-field scenes reminiscent of their win over Pakistan in 2007.
Meanwhile, England were left punch drunk by a bewildering evening although the warning signs were already there against the Netherlands.
Strauss and his underperformers will be eternally thankful that the ICC has rather ridiculously organised the tournament in such a way that teams can get away with two, or even three, defeats.
But such a long round-robin structure also opens the possibility of the agony being prolonged. Certainly, the athletic fielding and innings wins in the Ashes seem a lifetime ago, now.
Indeed, you really have to wonder who these bumbling amateurs are, and what on earth have they done with the real England?
WORLD CUP RESULTS/FIXTURES
GROUP A FIXTURES
AUSTRALIA + CANADA + KENYA + NEW ZEALAND + PAKISTAN + SRI LANKA + ZIMBABWE
| Date | Venue | Result |
| 20 Feb | Chennai | NEW ZEALAND 72-0 beat KENYA 69 by 10 wickets |
| 20 Feb | Hambantota | SRI LANKA 332-7 beat CANADA 122 by 210 runs |
| 21 Feb | Ahmedabad | AUSTRALIA 262-6 beat ZIMBABWE 171 by 91 runs |
| 23 Feb | Hambantota | PAKISTAN 317-7 beat KENYA 112 by 205 runs |
| 25 Feb | Nagpur | AUSTRALIA 207-3 bt NEW ZEALAND 206 by seven wkts |
| 26 Feb | Colombo | PAKISTAN 277-7 beat SRI LANKA 266-9 by 11 runs |
| 28 Feb | Nagpur | ZIMBABWE 298-9 beat CANADA 123 by 175 runs |
| 1 Mar | Colombo | SRI LANKA 146-1 beat KENYA 142 by nine wickets |
| 3 Mar | Colombo | PAKISTAN 184 beat CANADA 138 by 46 runs |
| 4 Mar | Ahmedabad | NEW ZEALAND 166-0 bt ZIMBABWE 162 by 10 wkts |
| 5 Mar | Colombo | SRI LANKA 146-3 v AUSTRALIA (No result - rain) |
| 7 Mar | New Delhi | CANADA 199-5 beat KENYA 198 by five wickets |
| 8 Mar | Kandy | NEW ZEALAND 302-7 bt PAKISTAN 192 by 110 runs |
| 10 Mar | Kandy | SRI LANKA 327-6 beat ZIMBABWE 188 by 139 runs |
| 13 Mar | Mumbai | NEW ZEALAND 358-6 beat CANADA 261-9 by 97 runs |
| 13 Mar | Bangalore | AUSTRALIA 324-6 beat KENYA 264-6 by 60 runs |
| 14 Mar | Kandy | PAKISTAN 164-3 bt ZIMBABWE 151-7 by seven wkts (DL) |
| 16 Mar | Bangalore | AUSTRALIA 212-3 beat CANADA 211 by seven wickets |
| 18 Mar | Mumbai | SRI LANKA 265-9 bt NEW ZEALAND 153 by 112 runs |
| 19 Mar | Colombo | PAKISTAN 178-6 beat AUSTRALIA 176 by four wickets |
| 20 Mar | Kolkata | ZIMBABWE 308-6 beat KENYA 147 by 161 runs |
GROUP B FIXTURES
BANGLADESH + ENGLAND + INDIA + IRELAND + NETHERLANDS + SOUTH AFRICA + WEST INDIES
| Date | Venue | Result |
| 19 Feb | Dhaka | INDIA 370-4 beat BANGLADESH 283-9 by 87 runs |
| 22 Feb | Nagpur | ENGLAND 296-4 bt NETHERLANDS 292-6 by six wkts |
| 24 Feb | New Delhi | S AFRICA 223-3 bt WEST INDIES 222 by seven wkts |
| 25 Feb | Dhaka | BANGLADESH 205 beat IRELAND 178 by 27 runs |
| 27 Feb | Bangalore | INDIA 338 tied with ENGLAND 338-8 |
| 28 Feb | New Delhi | WEST INDIES 330-8 bt NETHERLANDS 115 by 215 runs |
| 2 Mar | Bangalore | IRELAND 329-7 beat ENGLAND 327-8 by three wickets |
| 3 Mar | Mohali | S AFRICA 351-5 bt NETHERLANDS 120 by 231 runs |
| 4 Mar | Dhaka | WEST INDIES 59-1 beat BANGLADESH 58 by nine wkts |
| 6 Mar | Chennai | ENGLAND 171 beat SOUTH AFRICA 165 by six runs |
| 6 Mar | Bangalore | INDIA 210-5 beat IRELAND 207 by five wickets |
| 9 Mar | New Delhi | INDIA 191-5 beat NETHERLANDS 189 by five wickets |
| 11 Mar | Mohali | WEST INDIES 275 beat IRELAND 231 by 44 runs |
| 11 Mar | Chittagong | BANGLADESH 227-8 beat ENGLAND 225 by two wickets |
| 12 Mar | Nagpur | SOUTH AFRICA 300-7 beat INDIA 296 by three wickets |
| 14 Mar | Chittagong | BANGLADESH 166-4 beat NETHERLANDS 160 by six wkts |
| 15 Mar | Kolkata | SOUTH AFRICA 272-7 beat IRELAND 141 by 131 runs |
| 17 Mar | Chennai | ENGLAND 243 beat WEST INDIES 225 by 18 runs |
| 18 Mar | Kolkata | IRELAND 307-4 beat NETHERLANDS 306 by six wkts |
| 19 Mar | Dhaka | SOUTH AFRICA 284-8 bt BANGLADESH 78 by 206 runs |
| 20 Mar | Chennai | INDIA 268 beat WEST INDIES 188 by 80 runs |
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