Tonight will bring a huge contrast as the Bantams head to the smallest stadium in the Football League but the midfielder insists he could not be happier.
“I am very much enjoying my time here,” said the Scot, brought back to Yorkshire by David Hopkin after a two-year spell north of the border with Ross County. “I was out of contract and your faith wavers a little bit.
“It is tough watching Soccer Saturday (on Sky Sports) every week. This move is one I liked and believed I could get for a good few months. I live in Barnsley and my little boy is based there. I wanted to get back to him.
“I am very fortunate to be in this position but I believed in my ability to get the deal. I was training with Barnsley Under-23s in the summer under Martin Devaney. He was really accommodating but it was a bit stop-start. They helped me and kept me reasonably fit for when I got my opportunity here.”
O’Brien’s arrival at Valley Parade came just a few days into the reign of David Hopkin.
The new City head coach had identified a need for an on-field leader and the 31-year-old play-maker, who had four years at Oakwell before leaving in 2014, fitted the bill.
“I don’t think 31 is old,” said O’Brien, whose last start for Ross County before signing for Bradford had been at Celtic Park in March. “But when you are out of contract, 30-plus and you have been in Scotland for 18 months then it can be difficult to get back down to England.
“I was a bit baffled by some of the responses I got. It got to the stage where I could not even get the clubs that I didn’t want to go to! I kept saying to my agent, ‘Just get me in the door somewhere’.”
As for tonight’s trip to AFC Wimbledon’s homely 4,760 capacity stadium, O’Brien added: “I have been before but had an absolute stinker. I was with Shrewsbury and I got hooked at half-time so it is not a lucky ground. But we have confidence.”
Last six games: AFC Wimbledon DWLLLW, Bradford City LLLLDD.
Referee: A Young (Cambridgeshire)
Last time: AFC Wimbledon 2 Bradford City 1; December 23, 2017; League One.