Crystal Palace supersub Phillips hits that landmark in July and he could be the oldest outfield player in the top flight next season, four months ahead of Ryan Giggs, if they beat Watford, his first League club, in the £110million duel on Monday.
Phillips has only known Championship play-off heartbreak in three previous finals with Sunderland in 1998, West Brom in 2007 and Blackpool last year.
But Wembley is now the temple where Eagles dare to dream.
And if Phillips, 284 career goals and counting, can make it fourth time lucky in club football’s richest fixture, he will be the happiest KP in England this summer – no matter how many runs Kevin Pietersen might score in the Ashes series.
Phillips, who hit the first of his eight goals on loan from Blackpool in the 2-2 draw at Watford in February, said: “I’ve been to three play-off finals at Wembley with three different clubs and lost them all. People say it’s the best way to go up, but as I know only too well, it’s also the hardest defeat to take.
“You play for an extra three weeks when everyone else is on the beach and put in all the hard graft but when you lose, all that effort has been for nothing.
“In two of those three finals, the better team lost. Blackpool deserved better against West Ham last year and in 2007, when West Brom lost to Derby, we felt hard done by as well.
“And my other play-off final, at the ‘old’ Wembley, happened to be one of the most amazing football matches I’ve ever been involved in (Sunderland were pipped in a penalty shoot-out by Charlton after an epic 4-4 draw).
“When I was growing up I used to dream of scoring at Wembley and I went into that game under extra pressure because I needed one goal to beat Brian Clough’s post-war goal-scoring record for Sunderland.
“I had 40,000 people, one half of the stadium, singing my name when I did it and 35 goals in a season made me feel 10ft tall. But the bottom line is that we lost and 15 years later I’m still waiting for the play-offs to be kinder to me.
“That’s why I’ve been telling the younger lads to make sure they enjoy the occasion and to take it all in, because these big games come and go so quick and you might never get another chance to play in one.
“Last year, after Blackpool lost, I did look back as I left the pitch and wondered if that was my last time at Wembley as a player. When you are in your late 30s and you know your career is not going to last forever, you treat every game as if it were your last.
“I’ll be turning 40 in the summer, so to get back-to-back appearances in the play-off final, with so much at stake and the financial rewards involved, is pretty remarkable. All I ask this time is for a different outcome.”
Phillips, reunited with Ian Holloway after working with the Palace manager at Blackpool, where they were the Tangerines’ darling clementines, is happy with his role as an impact player on the bench but has not committed himself to any club beyond the summer.
He had “an informal five-minute chat” with Holloway about extending his stay in south London, but added: “There’s no need to go chasing new contracts or anything – let’s just see where we are after Wembley and let events take their course.
“But what I will say about Ollie is that I’ve never come across a person who is so passionate or enthusiastic about the game. He took a bit of criticism at Blackpool for being too gung-ho in the Premier League but tactically he is cute and the players all know their jobs.
“Our win at Brighton was no accident – we outwitted them tactically and in the end they ran out of ideas. That was down to the manager’s game plan.”
Since former Watford manager Glenn Roeder, who once described him as “the best 10 grand I ever spent”, plucked Phillips from non-League obscurity at Baldock Town in 1994, KP has returned to haunt the Hornets by scoring League goals against them for Sunderland, West Brom, Birmingham, Blackpool and Palace.
Phillips was almost apologetic about it, saying: “I’ll always have a soft spot for Watford because they were the club who took a chance on me. I owe Watford a hell of a lot – they made my dreams come true.
“If I score on Monday, I hope Watford fans accept that it’s nothing personal and what will be, will be. But I’m owed a happy ending at Wembley before I call it a day – somehow my career won’t feel complete without it.”