'Linfield are going to be fitter and sharper,' insists O'Brien
It's the rematch of the two champions on the island of Ireland after Shels prevailed in the July opener.
That Champions League path victory afforded them ties against Qarabag and Rijeka that ultimately resulted in defeats but this fallback to be part of the 36-team league phase was there to be activated.
That they're facing the same team twice is a quirk of the competition but over the two legs, firstly at Tolka Park and then Windsor on Thursday week, Shels are favourites.
In the favour of Linfield is the fact they're now in-season, compared to the initial match, and David Healy's side rock into the playoff on the back of Conference League wins over Lithuanian champions Zalgiris and Vikingur Gøta from Faroe Islands.
Victory would mushroom Shels' prize-money pot and guarantee six games between October and December.
'Seán has been back on the pitch,' O'Brien said of Boyd, whose calf strain forced him out of the first leg in Rijeka, which Shels came from behind to win 2-1.
'It's an impact sort of thing with him and there's that sort of impact there tomorrow, if needed.
'We signed Jack in this window and he's been training the last 10 days. They're all raring to go.
'I've always said these ties are four halves of football and there's only two in the first leg.'
O'Brien got to see Linfield in action last Thursday; a screamer by Kieran Offord set them on their way to beating Vikingur.
'Linfield are a good team,' said O'Brien.
'We've been obviously watching them since we last played them and most of them played against us.
'They've not changed the way they play but could change it again. They went with two strikers last week.
'They're going to be fitter and match sharper. We're in for a tough game.'
O'Brien insists the financial rewards for the club, players and staff are not a distraction.
Prestige from making history as the first Shels team to emerge from the qualifying rounds trumps monetary rewards.
'I suppose it is,' when asked about this being the biggest game in the club's history, stretching back to 1895.
'When you step away from it and you look at it and think, what's at stake? For me as manager and the lads as players, you don't wake up every minute of the day, going on the training pitch thinking, 'Jesus, this is the biggest game we've ever played.'
'If that was the case, you wouldn't be able to play. That's not what it's about.
'It's about concentrating on your performance and what has got us to where we are.
'The main thing is coming back into the dressing room with no regrets after the game.'
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