Laughing all the way to the bank is not quite appropriate given the sad mess in which Portsmouth fans find their club – and surely it is not such a bet that would be taken within the confines of that historic city – but non-Pompey fans would at the very least have a spring in their step. That special campaign began innocuously enough, as Pompey traveled to Championship strugglers Ipswich Town in the third round. Kind draws followed, with Plymouth Argyle visiting Fratton Park before a journey to Deepdale. Both ties saw Pompey heavily thanking Lady Luck as Paul Sturrock, then manager of the Pilgrims, bemoaned two strong penalty claims going unpunished by the referee, before Preston wondered quite how they exited the famous Cup after laying siege to Pompey’s goal only to come unstuck with an unfortunate late own goal.
As in any cup triumph for underdog sides, Portsmouth needed this luck to stay with them. While they were beating Preston North End, Liverpool lost at home to Barnsley while the tie of the round saw Arsenal thumped 4-0 at arch-rivals Manchester United. When the draw was made for the quarter-finals Portsmouth’s luck seemed to have ran out as they were lined up as the next to be put to the sword by Sir Alex Ferguson’s men. Far from running out, their luck was just beginning. United pounded Portsmouth’s goal, creating chance after chance as they went all out for glory. David James made a string of outstanding saves, Cristiano Ronaldo had a penalty claim turned down, Glen Johnson and Sylvain Distin both cleared efforts off the line and Patrice Evra hit the post with a fierce drive. On any other day United would have won by four or five, but not that day. That was the day when Portsmouth FC stood tall and demanded with their collective will and desire that Lady Luck smile upon them. When Milan Baros was fouled by Tomasz Kuszack in goal, it was clear that she had heard their call. They walked away from Old Trafford with a semi-final place against West Bromwich Albion assured, and from then on they became favourites.
Looking back on that glorious day at Wembley, any Portsmouth fan will tell you that it was their destiny and that they wish that they would have placed a small fortune on them lifting the trophy before the third round draw was made. Then, at least, they could go some way to helping their beloved team out of the financial quicksand in which it is entrenched. Of course, hindsight is a wonderful thing. The key to foresight in betting terms is to believe in the underdog, believe in the little guys in life. As Portsmouth revealed to us all in 2008, luck can travel with you. The shame is that for them, at least, their journey together appears to have come to an end.