But tomorrow his focus is on the similarly-clad Cherry Orchard.
An FAI Intermediate Cup final with Avondale at Turner’s Cross (3pm) exceeds all expectations made when coach ‘Toccy’ and manager Paul Doyle inherited a team just relegated from the Leinster Senior League’s top flight.
With their revamped Orchard outfit on course for promotion back to the top-tier at the first attempt, O’Connor insists this run to the final, along with the possibility of landing an Airtricity League giant in Monday’s FAI Ford Senior Cup third round draw, are ‘bonuses’.
However, given his own penchant for the big occasion — his goal in the 2001 FAI Cup final earned Bohemians their first double for 73 years — O’Connor will cut an inspirational figure in the Orchard dressing room as his charges look to defy the odds.
“The advice I’ll be giving our lads is to not let this occasion pass them,” says the 44-year-old, who claimed the first of three Premier Division winners’ medals in 1990 under Brian Kerr at St Patrick’s Athletic.
“Avondale’s edge over us in experience makes them favourites and so be it. That won’t affect our team; they’ll play without fear and won’t come under any pressure from Paul or I on the sideline.
“Whereas Avondale have lots of former Cork City players in their ranks, our group is comprised mainly of youngsters that have been introduced to intermediate football for the first time this season after spending a couple of years at League of Ireland reserve level.
“Apart from the McNevin brothers, Paddy and Alan, virtually all our squad are sampling their first big national final. That inexperience can be a blessing in my opinion. Reputations don’t count for much to our players — as they’ve shown by taking some big scalps along this route to the final.”
Last time on Leeside, just three weeks ago, the team from Ballyfermot overcame Cobh Ramblers to book that coveted berth amongst the big boys in the FAI Cup draw. ‘Toccy’ expects a throbbing Turner’s Cross, populated almost entirely by home fans, to provide a more demanding setting this time round.
“I hold great memories of playing against Cork City at Turner’s Cross but it is one of the toughest grounds in the country to come away from with a result. Despite that, I always found the crowd to be fair.
“Having the home crowd behind them gives Avondale an advantage but our lads will relish playing in such a quality ground.”
Win, lose or draw, O’Connor and Doyle can feel proud of leading Orchard to the club’s first Intermediate final for nine years.
Having first worked in tandem at Leinster Senior League club Dublin Bus before spending 2008 in charge of the Bohemians reserve team, the duo have hit the ground running in their latest assignment.
“I enjoyed my time with Bohemians working with Pat Fenlon, who I’d played alongside for St Pat’s and Bohemians,” explained O’Connor.
“Still, work and family commitments meant I needed to step away after the first season. When Paul (Doyle) was appointed to the Cherry Orchard job at the start of the season and brought me on board as coach, we knew there was a lot of change needed.
“The team which had been relegated wouldn’t have been strong enough for promotion, so we signed five lads from the Bohemians team we’d previously managed. More players were brought in and things took off.
“It’s different to senior football; fellas might miss training because of their job or could be unavailable for a weekend match to attend a stag do. The commitment is there from players but not to a career level it is at League of Ireland level.”
The honorary member of Bohemians’ ‘Hall of Fame’ scooped his last piece of silverware as a player in 2003 as part of Dublin City’s victorious First Division team. A winner’s medal tomorrow would be especially cherished.
Should success be achieved at the Cross tomorrow, O’Connor will cherish the medal he receives and allocate a special place for it in his household. “I don’t know where the medals from my playing career are,” he said. “I think they might be in my mother’s house but this one will stay in mine.”