For one set of fans, the Championship play-off final will bring a euphoric rise back to the Premier League.
For losing supporters, a desperate summer reflecting on missed chances and the prospect of another season in the Championship is likely to follow.
Smith said there will not be added pressure on Grealish, a boyhood Villa fan and the teams talisman, to play well against Derby. That is something right from the off we have played down, the former Brentford manager said. It is not about one person or pressure, it is about the team. If players perform as a team you have more chance. It is not down to Jack Grealish. Yes, Jack Grealish has got that little bit of brilliance but so has John McGinn and Tammy Abraham, [Anwar] El Ghazi and Tyrone Mings.
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Dubbed the richest game in football, with victory worth an estimated £170m, Mondays showpiece sees Aston Villa and Derby County go head-to-head under the Wembley arch.
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Its a meeting of big clubs with loyal fan bases, yet they come from two very different cities with contrasting football cultures. So how are the supporters feeling?
With five appearances in the last 13 seasons, Derbys experience of the play-offs is eventful to say the least.
Their Pride Park home sits on the outskirts of a small city rich in industrial and engineering heritage, with Rolls-Royce and Bombardier employing thousands in the area.
Derby is a one-club city and Frank Lampards team have flourished this season despite uncertainty over their ownership.
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Jamie Thrasivoulou is a lifelong fan and poet for the club. His poem We Are Derby will be broadcast around Wembley ahead of the final.
“It will be off the scale if we go up this season, I think it will change everything,” said the 35-year-old.
“It is happening at such a good time. You walk around and talk to people and see all of the activity on social media and everyones the same.
“I think itll be like nothing ever before because of the way it has all happened, with the victory over Leeds and the way the fans have taken to Frank Lampard.
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“People have been talking about the football more than I can ever remember before and there has been such a buzz around the city.”
Derbys most recent play-off victory came in 2006-07 – the first Championship final at the new Wembley. They beat West Brom 1-0 courtesy of Stephen Pearsons second-half winner.
That would make any prospective move for the Villa loanee unlikely, with the club unable to add to their attacking ranks to replace the striker ahead of the season.
“There were loads of people in the streets and everyone was so happy because we were in the Premier League, despite not playing very well in the final.”
What was an incredible high would ultimately be brought crashing back down with a dismal season in the top flight. Derby finished with 11 points and one solitary win, against Newcastle in September 2007, a record low that still stands today.
“We won’t put any pressure on any individual and talking to Jack he doesn’t feel that either, he has relished being the captain of Aston Villa and is looking forward to the game and hopefully getting that win.”
Lynn Hemsworth, who is chairman of the Derby County Supporters Trust and has been attending games home and away for 45 years, said the level of support from the crowd never dropped in that infamous top-flight campaign despite the poor results.
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“The mood had gone down by Christmas because we hadnt been picking up results but once people came to realise the inevitable (relegation) then they just started to enjoy it,” she said.
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“The supporters had fun and really got behind the team. They kept turning up and didnt boo or give them a hard time. And at the end of the year the supporters were given the clubs Player of the Season award.”
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Fast-forward to 2013-14 and it was Derbys turn to feel the full force of a Championship play-off defeat.
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“To lose that the way we did was heartbreaking having been the better team for most of the match,” Jamie added.
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“Being at Wembley that day was awful and I think it took us a few years as a club to really recover from it. Its pretty bad in the memory and I think its one everyone hopes well lay to rest on Monday.”
Derby have since reached the play-off semi-finals twice more before this season, losing to Hull City in 2016 and Fulham last year.
The play-offs are a relatively new experience for Villa fans having featured in the first 24 of the Premier Leagues 27 campaigns since its launch in 1992.
Following relegation from the top flight in 2016 and consolidation the following season, they reached the play-off final last year but lost to Fulham.
Villa fan Mitchell Booth from Longbridge in Birmingham compared the loss to going down and was taking nothing for granted this time around.
“After playing the extra games and coming so close it felt like going through relegation again,” the 25-year-old said.
“We were in a downward spiral in the three or four years leading up to the relegation so it would be great to have something to look forward to if we do get promoted.”
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It set up a tantalising local derby against West Brom in the play-off semi-final which Villa came through on penalties at The Hawthorns.
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While most of Derby is united behind the Rams and their long-standing feud with Nottingham Forest, Villas rivals are much closer to home.
The West Midlands is a hotbed of established top level clubs including Wolverhampton Wanderers, the Baggies and Villas fierce rivals Birmingham City.
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With the two teams grounds less than four miles apart, Baggies fans have had to watch as friends, colleagues and family members celebrated Villas dramatic victory on 14 May.
Baggies supporter Will Matthews works with several Villa fans, including Mitchell, and has tried to shut out the noise around the final.
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“I grew up slap bang in the middle of Albion and Villa, so I know a lot of Villa fans and I dont exactly keep my mouth shut before games. I think Villa will win but I just hope Derby stuff them to be honest.”