Galway boss issues FAI Cup warning to players, outlines transfer window problems
Caulfield played and managed in the Munster Senior League after a successful League of Ireland career at Cork City.
So he knows that Tolka Rovers will be up for the game, particularly as Galway haven't won in their last four outings and haven't scored in their last two.
'I think it's a great game for Tolka Rovers, coming from non-league football, that I've been in for a long, long time,' said the former Cork City boss.
'Tolka Rovers are a massive club in non-league, and I think it's a glorious opportunity for them, and they'll see it that way.
'We will show them all the respect. The bookies will probably put us as favourites, but we need to play well and the last number of weeks we haven't played well, and if we don't we'll be knocked out.
'I think the brilliant thing about the Cup is a non-league team, while they might be out of season, in my experience in non-league with Avondale, we might have been out of season but we were still very fit lads.
'Okay, not maybe to the level of League of Ireland, but we were still fit lads and I'd expect the same from Tolka.'
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Caulfield has been busy in the transfer market already this summer, bringing in Trinidad and Tobago striker Malcolm Shaw, English midfielder Axel Piesold, and former Shamrock Rovers and Cardiff City midfielder Aaron Bolger.
He has lost in-form striker Moses Dyer, while the end of Cian Byrne's loan spell saw him line out for Bohs on Friday against his old teammates.
The Galway boss is eager to do some more business, but says it's a tricky time of year to bring in players and expect them to hit the ground running.
'It's difficult mid-season,' he said. 'I'll always say it's hard for us to get players to Galway.
'The problem for us at the moment is a lot of them haven't played since May. If we can get to the middle or end of August, fine, but it's that conundrum where we are trying to rush boys in and you have lost players who have played the last six or eight months and who were flying fit.
'These lads are very good, you can see that, but if you are that little bit off, you get done.'
Despite his rustiness, Shaw showed some good touches at Dalymount Park, and wasn't far off scoring with an overhead kick in the first-half.
'He has a lot about him, to be fair,' said Caulfield. 'We see him in training, we see him finishing and he just needs something to go in for him.
'But it is difficult. When it doesn't happen, everyone keeps referring to (Moses) Dyer. But to be fair to Malcolm, if he was here since January, with a full pre-season in him, I have no doubt that he would have a number of goals.
'He will score goals, I have no doubt about that. But it's just one of those where it's a difficult situation and we just have to dig in.
'Some of our more experienced players are probably going through a bit of a rocky patch, and that can happen.'
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