The 1998 First Division playoff final is considered to be one of the greatest matches to have been played at the old Wembley, with Charlton coming out on top 7-6 on penalties following a 4-4 draw after extra time, and now the sides do battle once again on the big stage.
This will be Charlton's first taste of a playoff final since that epic clash with Sunderland 21 years ago. Their only other such fixture came in 1987 when beating Leeds United in the Second Division final after being taken to a replay.
The prize may not be as big this time around, with the finalists now languishing in the third tier of English football, but for both sets of supporters this is a huge occasion - a chance to move back to within one promotion of the big time.
Charlton finished three points better off than Sunderland at the end of the regular League One campaign, accruing 88 points to narrowly miss out on automatic promotion.
Lee Bowyer's men had been chasing down second spot along with Portsmouth and Sunderland, but Barnsley pipped them to the post to join Luton Town in next season's Championship.
A 4-0 victory over Rochdale on the final day of the season ensured that Athletic finished above Portsmouth and Charlton in third, though, setting up a favourable playoff semi-final against sixth-placed finishers Doncaster Rovers.
Charlton ended the season 15 points better off than Doncaster but that, as we have come to find out down the years, ultimately counts for little when it comes to the end-of-season shootout.
Bowyer's side won the first leg 2-1 at the Keepmoat Stadium and led 3-1 on aggregate with two minutes of the second leg played, only for Rovers to produce a fine comeback to take the game to extra time.
A 4-3 penalty shootout win kept their hopes alive, though, and now Charlton supporters are preparing for their first trip to the national stadium since 'that' famous afternoon against Sunderland in the last millennium.
Including their semi-final triumph, the South London outfit have won five matches in a row and have lost just one of their last 17 games since the start of February, leaving them in perfect shape for this final outing of a campaign that could end on the highest of highs.
Recent form in League One (including playoffs): LWWWWW
Whereas Charlton are the third tier's most in-form side taking games over the past six weeks into account, Sunderland are at the opposite end of the table.
The Black Cats ended the regular season with one win from seven to miss out on automatic promotion by six points, but they put that disappointing run behind them by beating Portsmouth in the playoff semi-finals.
A little over a month on from losing to the same opponents in the EFL Trophy final at Wembley, Sunderland beat Portsmouth 1-0 at the Stadium of Light and then held on for a goalless draw in the return match to set up another trip to the capital.
Chris Maguire's volley just over an hour into the first leg settled the tie between the heavyweight League One clubs as a scrappy second leg that failed to live up to its billing, especially sandwiched between some thrilling ties elsewhere.
Sunderland therefore remain on course for an immediate return to the Championship, a year on from their second successive relegation being confirmed with a home loss to Burton Albion.
It recently emerged that the North-East outfit cost the club £20m in pre-tax losses and led to the loss of numerous jobs, not least behind the scenes and in the dugout.
Jack Ross was brought in from St Mirren and has gone the right way about guiding the Black Cats back into the second tier, even if the campaign has had a few lows, not least the shaky form to see out the campaign.
Ultimately, though, Ross is on course to achieve his target of getting Sunderland out of the division. However, they have failed to win either of their previous playoff finals, losing 1-0 to Swindon Town in 1990 and on penalties to Charlton in 1998 - a record Ross will be desperate to put an end to this weekend.
Recent form in League One (including playoffs): DDLLWD
Bowyer named the same starting lineup for both legs of the semi-finals against Portsmouth and could do the same again at Wembley.
Jonny Williams, who spent time on loan with Sunderland in their doomed 2017-18 campaign, is in contention to return to the side after being introduced from the bench against Portsmouth last week should Bowyer opt to change things around.
The same is true of Pratley, who made a telling impact from the bench in the semis. However, with a fully fit squad to choose from, Albie Morgan is expected to get the nod here.
Lyle Taylor has been directly involved in 32 goals in League One this season - 22 goals and 10 assists - which is more than any other player.
As for Sunderland, Aiden McGeady is back in contention after missing four matches with a foot injury sustained in early April.
McGeady has already netted once at Wembley this season, but he is unlikely to force his way straight back into the starting lineup.
Ross has a fully fit group to choose from, which could see him go with the same XI from the semi-final second leg against Portsmouth.
Charlton possible starting lineup:
Phillips; Dijksteel, Bauer, Sarr, Purrington; Morgan, Bielik, Cullen; Aribo; Taylor, Parker
Sunderland possible starting lineup:
McLaughlin; Matthews, Ozturk, Flanagan, Oviedo; Power, Cattermole; Gooch, Honeyman, Maguire; Wyke
Head To Head
Charlton have lost just one of their last eight meetings with Sunderland in all competitions, drawing half of those, with that solitary defeat coming on the opening day of this season's League One campaign - a 2-1 loss at the Stadium of Light.
Both teams have found the back of the net in eight of the last nine contests between Charlton and Sunderland in all competitions, the only exception being a 2-0 win for Charlton in the 2005-06 Premier League season.
We say: Charlton 1-1 Sunderland (Charlton to win on pens)
The side finishing fifth in League One - Sunderland this season - has not gained promotion via the playoffs since Barnsley in 2005-06. Furthermore, only Newcastle United (eight) are on a longer winless run in matches played at the old and new Wembley than the Black Cats, who have drawn two and lost four of their last six such matches, so we are backing Charlton to edge this one.