Then in the FA Cup he drew Chelsea, who go to Filbert Street this afternoon as favourites not only to win the match but the pot itself. Next he lost half his squad with injuries or suspensions. On Wednesday it got worse, psychologically at least, when a Chelsea player helped make England look ordinary. Yet O'Neill still says that if it had to happen, the timing of misfortune could not have been better.
Amiable whimsy is not altogether unknown to the former Irish international who for a long time ignored all the publicity about being one of football's bright young bosses and stayed at Wycombe because "I enjoyed being in from the beginning". His attitude to today's game, which most would see as the big one of the season, is that the outcome matters less than Tuesday's Coca-Cola Cup tie against Wimbledon (because that competition is only two games from Wembley), or next weekend's home Premiership match against Derby.
Overseeing Friday's training, O'Neill was continually joking about the sleepless nights he would have contemplating the selection of a team from 14 available players - including two goalkeepers and two first-year professionals. "I have to believe that it's a situation you very rarely encounter. At Premiership level you should hardly ever get four players suspended at the same time and all these injuries, but if you are a Premiership club you have to cope with that. But we don't seem to be in that ball game at the moment. If we survive this season, then I would hope we will have enough players to cope properly but now we've got the smallest squad in the Premiership and the situation has exposed us."
Two matches this season have given O'Neill an insight into the state of play in the Premiership and left him not knowing quite what to believe about the future. With last season's promoted clubs not doing too badly and none of the leading rich ones taking a hold at the top, there is a curious unpredictablity. He thought that losing to Newcastle after taking a 3-1 lead at St James' Park was "the most painful defeat I've ever had to suffer" but beating the amazingly resilient Wimbledon was an inspiration that surpassed dismissing Manchester United from the Coca-Cola Cup. It inspired him to believe that a squad he admits needs a lot of strengthening could nevertheless survive and even qualify for Europe.
O'Neill, a former European Cup winner with Nottingham Forest, badly wants the flavour of European competition, which is why he would be happy to cut his losses today. While not exactly playing for a draw ("I don't know any manager anywhere who can do that") he would not mind earning one, and then getting Emile Heskey, the raw, quick striker, and the experienced defender Matt Elliott back in action for a replay.
But the matter of again overcoming Wimbledon is paramount. Joe Kinnear, their manager, is certainly not underestimating O'Neill's chances. "His team has given us as many problems as any in the Premiership this season," he said.
O'Neill is not the sort to have nightmares, but his worst foreboding is to have Leicester dumped out of both cups and then suffer a fall in confidence in the league. "We have a situation in which heart and soul may not be enough," he admitted. With Steve Claridge running his socks down in every game and the defence often holding up against the best attacks, he might have been tempted to do a man-to-man marking job on Gianfranco Zola. "Trouble is I haven't got the man, but it's not all doom and gloom. It's fantastically exciting. It's the chance for us to prove that all that stuff about camaraderie means something." No team O'Neill manages will ever lack that.