It would certainly represent quite the achievement for the former Gosport Borough and Torquay striker-turned-manager, who never operated above League Two level in his playing days with the vast majority of his appearances coming at the higher end of the non-league pyramid.
But no matter if he is ever fortunate enough to walk out under the famous arch again, there will always be a 'special' national stadium moment which sticks with Sills.
In successive seasons with the Gulls, Sills, now 42, suffered FA Trophy heartache as his side went down 1-0 to Ebbsfleet in the 2008 FA Trophy final, only to return a year later and score as Torquay defeated Cambridge 2-0 in the Conference play-off final.
But it was the most ‘unexpected’ of his three Wembley appearances during a season-long stay with Conference South Gosport in which one of his fondest memories arrived.
Boro, then managed by Alex Pike, had defied the odds to reach the FA Trophy final where fifth-tier high-fliers Cambridge – who were eventually promoted - were the opponents.
It certainly wasn't a result to remember for Sills and his Gosport team-mates, who were defeated 4-0 on that March day in 2014, but the occasion provided a moment which will long be remembered among the Sills family.
He revealed: ‘I think the other experiences I had at Wembley, my oldest son (Ethan) was too young to remember, so the one with Gosport he was able to be my mascot with me as well on the day - that made it a lot more special.
‘Mick Catlin was assistant manager and had his grandchildren I think involved as mascots. I managed to walk out with my son as well so it was very special.
‘It was a good career (as a player), I played for some really good clubs, and was fortunate enough to play at Wembley three times - the Gosport one was definitely the least expected!
‘In the quarter-final we went up to North Ferriby in Hull - I think they were riding high at the top of the Conference North at the time - we managed to win that one, we beat Nuneaton away, who were in the Conference, and the Gosport v Havant & Waterlooville draw was destined.’
Sills ensured his name will forever be etched into Gosport folklore by netting all three goals in the club's two-legged FA Trophy semi-final triumph over the Hawks to reach that Wembley final.
He struck as Gosport drew 1-1 at Westleigh Park in the first leg, then went onto grab both goals in a 2-0 victory at Privett Park in the return fixture. And his crucial input across those two legs offers a perfect small piece of his playing career to reflect on.
Sills said: ‘It was a fantastic occasion (FA Trophy semi-final), brilliant for both clubs in terms of local interest. Luckily it was even better for us and myself with the goals as well - it always helps.
‘It was a great occasion, great day (overcoming Hawks) and just gave us a great day out at Wembley, which was always going to be a bit of a struggle, but it was always more about the occasion for the club at that time.’
Presently, Sills is cutting his teeth in his first managerial role with Wessex League Premier Division Hamworthy.
In his third season at the club after being appointed to the role in October 2019, the Dorset club are in a three-way tie at the top with PO postcode pair Horndean and Baffins Milton Rovers. They have also lost once in 23 league games, 2-1 at Baffins. As it stands, they are due to host the return fixture in their penultimate game of the season on April 2!
Hamworthy – who defeated US Portsmouth to lift the Wessex League Cup last May, Sills’ first major trophy as a manager - also have a home FA Vase fourth round tie (last 32) with Southern Counties East League outfit Glebe this Saturday. The following weekend they travel to Horndean for the two clubs’ first meeting of 2021/22.
But despite a playing career which saw him feature at Football League level and the top end of the non-league, Sills is refusing to make any bold predictions about how things could pan out for him in the dug-out.
‘Who knows? (making it to higher levels as a manager). You’ve obviously got to be ambitious, but the nature of football management is you have no idea what’s going to come the next Saturday, let alone try to plan out some sort of career,’ said Sills.
‘If it keeps going as it is then we’ll take Hamworthy on, hopefully, maybe up to a new level which would be good. Then who knows after that.
‘It’s very much focusing on having the most success we can this year, then after that we’ll see what happens.’