Ainsworth was part of a Preston squad beaten at the national stadium in the old Division Three play-off final in 1994. The team celebrating promotion that day was Wycombe.
Now Wanderers manager, Ainsworth wants Wycombe to win again.
“It’s an amazing irony really that both Wycombe and Preston are back at Wembley in their respective play-off finals,” said Ainsworth.
“On one hand I hope history repeats itself with Wycombe winning but on the other hand I hope that it doesn’t repeat itself with Gareth Ainsworth losing.
“One of those two scenarios is going to happen, I just hope it’s the first one.”
Ainsworth was 21 years old at the time of that defeat with Preston and admits the game, which Wycombe won 4-2, and the occasion passed him by.
Ainsworth wants his players to savour the occasion against Southend and has reminded his players it may be the only chance they get to play at Wembley.
He said: “When you’re young you think you’re going to get there more times than you do in your career but in 26 years of being in football I’ve only been to Wembley once, so take heed people because it doesn’t come round very often.
“It’s a special occasion and I think that when you’re older you take more in anyway. When you’re younger you let things pass you by, and the defeat didn’t help either so maybe subconsciously I wanted to forget about it.
“I think a look around the stadium will help so we’re going to try and get there and make sure that when the players do walk out on the pitch it isn’t the absolute first time that they’ve done it.
“To prepare them is going to be important and also I don’t want anyone to be in awe of anyone or treating this game any different.”
Managing in a play-off final is new ground for Ainsworth, at the end of only his second full season in charge of Wycombe.
Southend boss Phil Brown, however, guided Hull to the Premier League via the play-offs in 2008.
Brown, who next weekend will turn 56, is keen to play that down though and instead concentrate on the job in hand.
“It’s a big game and I think the disappointing part from the media is about my time at Hull City,” he said.
“There’s only one game I’m interested in this weekend and that’s Southend United versus Wycombe Wanderers. The stakes are high and may the best team win.
“We enjoyed some great scenes after the game against Stevenage the other night but I didn’t celebrate because the job is only half done.
“There is still one more very tough game for us to come against a very good Wycombe side and I’ll only start to celebrate if we win that one. Saturday’s game, nothing else, is the focus.”