It's been a long time coming. It was in 2008 that Montreal first qualified for the tournament. At the time, Montreal was in the second division USL, but made it to the tournaments' group stage by winning the Canadian Championship.
Very little stock was put into a second division side competing against the best teams in CONCACAF.
And yet the Impact made it to the quarter finals, beating Santos Laguna in front of 55, 571 fans at the Olympic Stadium - a match which has been engrained in the culture and history of the club and supporters ever since. They lost the second leg in Mexico, but that was enough to get a taste for the competition.
And on Wednesday night, the Montreal Impact will get their second chance.
San Jose is having a polar opposite season to last year where they won the Supporters' Shield by finishing first in the MLS.
They currently sit in 8th place in the west with a record of 8-6-9, but are still only 3 points off the 5th and final playoff spot in the west. A testament to how competitive that conference really is this year.
Chris Wondolowski is also having a Dr. Jekyll and Mr. Hyde kind of season when compared to last year's goal tally of 27 in 32 games. He currently sits with 8 goals in 23 games.
Goal scoring has been a real problem - especially away from home - for the San Jose Earthquakes where they've only managed to find the back of the net 7 times so far this season.
Montreal would do well not to pay too much attention to these stats as this is a team that is always dangerous and capable of changing a game in an instant. That was made evident when San Jose got a 91st minute equalizer against Montreal back in May. The Impact was going into the 2nd half of the game with a 2-goal lead.
Defensive responsibilities and a strong possession game will be key to getting the first 3 points in the group.
It's possible that we'll be seeing the debut of one or both of the Impact's new signings. Designated Player Hernan Bernardello is the more likely of the two , having already made it to the substitutes bench against DC, over the weekend.
Whether it's a 4-3-3, 4-2-3-1 or 4-4-2, Bernardello's experience as a defensive midfielder will be key in each scenario. Getting him minutes now will only help his integration into the team before the congested schedule that lies ahead.
Alessandro Nesta is back in training this week after missing the DC game. It seems that the Italian veteran will get the start but it is still unknown who his partner will be.
Adrian Lopez is a possibility, although his fitness level may not be quite match ready for a start on Wednesday.
The start of the Champions League brings with it the busiest period in the schedule for the Impact this year.
August will see them play 7 games, where September will bring another 6. Rotating the squad and using all the players at his disposal will be key for Marco Schallibaum. The Swiss head coach will need to juggle with his lineup if he expects to progress from the CL group stages while also making the MLS playoffs.
Blake Smith had been put on notice last week that he may get a start at any time. It would be easy to argue that after his recent performances, a start on Wednesday would be deserved.
Players like Dennis Iapichino and Collen Warner could also see starts, where guys like Maxime Tissot, Wandrille Lefevre and Karl W. Ouimette will also be in the mix.
The match against the Chicago Fire , on Saturday, will be very important for the eastern conference standings. So you can expect to see a lot of minutes being divided amongst these types of players on Wednesday and in the weeks to come.
The Impact travel to Guatemala next in the Champions League on August 21st where they face CD Heredia who made it into the competition by finishing Runners-up in their 2012-13 domestic season.