First up, perennial League 2 strugglers Albion Rovers will visit the Falkirk Stadium on Tuesday night.
This is the “easiest” match on paper but the men from Coatbridge have the players to hurt Falkirk if they are not careful.
Scott Roberts comes in from Stirling Albion this summer while winger Aaron Lynas and veteran striker Ryan Stevenson will both work the Bairns defence hard.
All the same, victory in their opening game is a must or their qualification chances could end before they really begin.
Drawing a group without a Premiership side was a huge boost for Falkirk but Hamilton Accies still boast a squad full of top level talent despite their relegation last season.
They have strength across the park with the likes of Hakeem Odoffin in defence and David Templeton in attack.
The group stage format usually means a team can afford one slip up and still qualify, this would be the match to do that in but if Falkirk go in to it with no fear they have every chance of a positive result especially with home advantage.
Edinburgh City are perhaps the most interesting test of the three.
The Citizens have shown over their quality in League 2 over the past few years and have gradually built up a squad that could easily hold its own a division higher.
Falkirk will still start the match at Ainslie Park as favourites but, similarly to the Bairns facing Accies, City will look at this as a tie they can get a positive result from with a good performance.
Finally it’s Championship side Ayr United at Somerset Park to close out the group.
The Bairns and the Honest Men are hard to separate on paper and most will predict a tight contest.
Ayr, with home advantage, will be favourites but this match has the potential to have the often clichéd “cup final feel” if both go in to it with a chance of qualification.
That means it will be all to play for in a game where a strong performance could very well secure a knockout stage spot for the Bairns.