But Sir Alex Ferguson will be wary of the man standing in his way of an unprecedented quintuple - Manchester United's cup nemesis Harry Redknapp.
Three times with three different teams, Redknapp has sent the Red Devils tumbling out of the FA Cup and now he is aiming to help Tottenham defend the Carling Cup.
Twenty five years ago, Bournemouth claimed a 2-0 win over United at Dean Court, while five years later, with Ferguson in the visiting dugout, the Cherries forced a replay after a 1-1 draw on the south coast.
Redknapp believes, had his Bournemouth side won the replay at Old Trafford, Ferguson's reign as the most successful manager in British football might never have happened.
"It might have done," he once said.
"We played fantastic, Bournemouth, and should have beaten them. But from United's point of view it's lucky that they didn't because he has gone on to become one of the all-time great managers."
West Ham beat United at Old Trafford in 2001, while last season Ferguson's side were vanquished again, when eventual champions Portsmouth won the FA Cup quarter-final clash.
However, the Scot exacted a measure of revenge by leading a depleted United side to a 2-1 victory over Spurs in the FA Cup fourth round on January 24, ending Redknapp's hopes of winning that particular trophy in successive seasons with different clubs.
Now Ferguson is on the cusp of a haul of five trophies in one season - the Club World Cup has already been claimed, while United have the Premier League, the Champions League and the FA Cup in their sights - but Redknapp could halt the bid in its tracks.
The duo began their managerial careers at either end of the country and at the bottom end of the spectrum - Ferguson with East Stirling, Redknapp with Bournemouth.
Ferguson, via St Mirren and Aberdeen, has gone on to create a dynasty of unrivalled success at United, collecting 31 major trophies, including the Carling Cup on two occasions since he took charge in November 1986, while last season's FA Cup success with Pompey is Redknapp's only winners' medal to date.
Despite the disparity in the medal collections, the duo are two of the most respected leaders in the history of football.
Ferguson is feared and revered for his longevity, while Redknapp's success can be measured by his standing as one of the most coveted bosses in the game.
When Redknapp felt he was undermined during his first spell at Pompey, frustrated at the appointment of Velimir Zajec as director of football, he left for Southampton. Redknapp returned to Fratton Park after one season with Saints and was then selected by Spurs as the man to galvanise them.
Upton Park is the furthest north Redknapp has travelled as he revolutionises clubs, while Ferguson has again and again worked his magic in reforming United, nurturing youngsters and luring players from across the globe.
Many believe the 67-year-old's current crop of talent is his best yet, better even than the double winners of 1994 and 1996 and the treble winners of 1999.
And it is certain no quarter will be given between these two pensioners in their battle at Wembley, despite the final falling a day before Redknapp's 62nd birthday.
Another certainty is that whoever claims the trophy will leap down the touchline with the vigour and athleticism of a virile youth in defiance of their years.