An encounter with the champions and the favourites for the title made it a baptism of fire for new Hibs coach Mark Miller who was making a return to club management following his lengthy spell as a key member of the MFA technical team.
Their confidence high after two wins from their opening two matches, Hibs got Miller's reign off to a positive start, their 1-1 draw with Valletta enhancing their fans' optimism that the former Malta U-21 mentor is the right man to revive the team's fortunes.
Miller had no qualms about the result of Monday's game.
"We tried to win, we didn't go out to defend," he told The Times.
"The team showed a positive attitude throughout and probably, the draw was a fair outcome. I thought we had the better chances but it was a tight game against an experienced Valletta side."
In the lead-up to Monday's game, Miller opined that a clash against a City team boasting the strongest squad in the Premier League would provide a good indicator as to how far Hibs can go this season.
The Paolites passed their first real test but Miller prefers to look at the broader picture instead of narrowing his focus to just one match.
"Every game is difficult and every game has its own story," Miller said, invoking two old football clichés.
"We face Ħamrun next and it will be another tough match because they desperately need the points.
"As for Valletta, if you look at their bench on Monday, you get an idea of how strong their squad is. The likes of Cleaven Frendo, Dyson Falzon and Josef Mifsud were substitutes and these are players who can play in anybody else's first team.
"At the moment, my bench is made up of U-17 and U-18 players. If our 12 to 13 first-team players manage to stay fit, we can compete with Valletta but I know that the size of the squad does make a difference in the long run.
"I need three more experienced players to challenge for the honours. Our young players are very talented but they need time to develop."
Hibs' unbeaten start has heightened expectations among their supporters but Miller has been in football long enough to know that three good results at the start of the season offer no guarantee for success.
"It's still early," Miller, who has signed a four-year deal with Hibs, said. "If you lose two games, everything changes. The confidence of the players drops and suddenly your job becomes more complicated."
Although Miller's first official day of work with Hibs was Monday, September 8, it is an open secret that the Englishman assumed a leading role in the team's preparations for the new season and made some key decisions with regards to personnel.
While the release of Nigerian Uzeh Edafe and Abada Fish was widely expected, Miller's decision not to keep midfielder Pablo Doffo came as a surprise to many but in ushering the Argentine to the exit door, the new coach showed that he wanted to turn a new page.
Hibs have a new foreign line-up with Rumen Galabov, formerly of Pietá Hotspurs, the only one of the three with experience of local football. Uruguayan midfielder Christian Callejas and Cameroon's Alexis Tekumu Mbongo were signed after impressing during their trial with the club.
"What we've tried to do is bring in good foreign players who also have the right character," Miller said.
"We have also been working to help the older players in our team get their confidence back. We have also changed the team's playing style, we want to attack and the players are enjoying it."
Miller is enjoying the day-to-day nature of club coaching, having spent the previous eight years monitoring, assessing and training the country's emerging players.
"The two jobs are completely different," Miller said. "With the national teams, I was watching a lot of games and a lot of players. I only had the players for a short period of time before games and you only played a competitive match or two once every two or three months.
"At club level, the job is on a day-to-day basis. Because you see the players so often, they get used to you, so the challenge is to vary the training sessions and keep the players on their toes."
Miller's objective for the first year of his second spell as Hibs coach is to lead the team to a top-four finish.
"We will be very disappointed if we don't get into a top-four spot," Miller said. "That's our biggest aim this season. As I said, we still need to get in two or three players but I think we have what it takes to finish in the top four."