If you could peek into Marc Bergevin’s calendar, there would probably be several dates circled in red as milestones during the off-season. As the Montreal Canadiens’ general manager begins constructing the team for next season and beyond, here is a quick summary of the dates he will be planning around.

June 1: Last day to sign 2015 Draft selections playing in the CHL

The NHL Collective Bargaining Agreement has set different timelines for when you have to sign a draft pick by before they become eligible for unrestricted free agency.

In the case of players who play in the Canadian junior system, that timeline is two years after they’re drafted, therefore the players affected are those from the 2015 draft year.

That class yielded four such players: Noah Juulsen, Jeremiah Addison, Simon Bourque, and Matt Bradley. Out of this group, Bradley remains the only one that is unsigned, and it doesn’t look as though the Canadiens will want to offer him an entry-level contract despite ever-increasing offensive output from the forward.

This past season with the WHL’s Medicine Hat Tigers, Bradley recorded 34 goals and 77 points as a 19-year-old. He has suffered from bad luck with injuries since being drafted, like undergoing sinus surgery last year, usually timed with the Canadiens’ development camps so the coaches saw very little of him.

Bradley will likely return to Medicine Hat next season for his over-age campaign as an unrestricted free agent.

Expansion Draft

The NHL is expanding to 31 teams with the addition of the Vegas Golden Knights next season. Thus far they only have two players signed: former Montreal Canadiens tryout Reid Duke and rumoured free-agent addition Vadim Shipachyov. The expansion draft will allow them to add another 30 players to their roster, as every team must have one player selected.

Here is the calendar of events of the expansion draft:

June 17, 5 :00 PM ET : Submit protected list

: Submit protected list June 18-2 0 : Vegas can negotiate with any unprotected unrestricted or restricted free agent

: Vegas can negotiate with any unprotected unrestricted or restricted free agent June 20, 5 :00 PM ET : Vegas submits Expansion Draft selections

: Vegas submits Expansion Draft selections June 21: Announcement of selections

The Canadiens have some interesting choices to make when it comes to their protected list, with some of the bigger names risking selection including Tomas Plekanec, Nathan Beaulieu, Alexei Emelin, Jordie Benn, Brandon Davidson, Charles Hudon, Paul Byron, and pending free agents Andrei Markov and Alexander Radulov.

June 23-24: NHL Entry Draft

The NHL Entry Draft is being held in Chicago this year. Although the final draft order is not set until the playoffs conclude, the draft lottery did finalize the draft order for the first 15 teams, with the New Jersey Devils selecting first, followed by the Philadelphia Flyers and Dallas Stars. The Canadiens will first pick somewhere in the 18-24 range.

The Canadiens will only have five picks this year after trading away their fourth-round pick along with Greg Pateryn for Jordie Benn, their sixth-round pick along with Jonathan Racine for Nikita Nesterov, and their seventh-round pick for Winnipeg’s seventh-round selection in 2016 so that the Canadiens could draft long-term Swedish project Arvid Henrikson.

The Canadiens do have two second-round picks, including Washington’s from the deal that sent Lars Eller to the Capitals.

To summarize, the Canadiens are currently slated to pick once in the first round, twice in the second, once in the third, and once in the fifth, adding a total of five new prospects to their pipeline.

June 26, 5:00 PM ET: Qualifying Offers to Restricted Free Agents

Restricted free agents need to receive their qualifying offers by this date, otherwise they become unrestricted free agents and can sign with any NHL team as of July 1st. The Canadiens purged a lot of their RFAs last season, so it will be interesting to see what happens this summer. A qualifying offer is a simple formality to start negotiations with a one-year contract offer, and the signed contract can vary from that. Here is the complete list of players that would need to be qualified:

* arbitration eligible (explained further below)

June 30: Expiring Contracts

This is the official final day of the NHL season for contract purposes. With their contracts expiring, the following players are heading for unrestricted free agency:

Bobby Farnham

Brian Flynn

Dwight King

Andrei Markov

Andreas Martinsen

Steve Ott

Alex Radulov

The Canadiens can of course re-sign them at any point after they hit free agency, but if they re-sign them before July 1, they have the option of offering a maximum eight-year extension. After July 1, seven-year extensions are the maximum allowed duration, and can be offered by any team in the league.

Also on July 1, the Canadiens will lose the rights to Swedish defenceman Magnus Nygren who has played in Europe for the last three seasons, as he reached the unrestricted free agency age of 27.

July 1: Free Agency

Bergevin has always proven himself to be very conservative on this day, avoiding the inflated contracts that have doomed several other teams to terrible long-term deals.

Instead Bergevin focuses on team needs at depth positions, such as signing backup goaltender Al Montoya, defenceman Zach Redmond, and forwards Bobby Farnham and Chris Terry to provide depth for the organization after last season’s purge. Bergevin’s biggest splash on this day happened to be last season when he plucked Alexander Radulov out of the KHL.

Who will Bergevin target this season? There are a lot of older experienced players who would be looking for a final payout that the Habs might look to for leadership such as Joe Thornton or Patrick Marleau. There are some younger players who will be looking for a big payout such as T.J. Oshie and Nick Bonino. Bergevin went hard after Martin Hanzal at the trade deadline, but does he still want the big centreman after he fizzled out a bit with the Minnesota Wild?

In addition, there is the option, however rare, of putting in a hostile offer for another team’s restricted free agent. There seems to be an unspoken agreement between general managers that offer sheets won’t be made, however there are several players out there who might be just too attractive for Bergevin to shun convention, such a Leon Draisaitl of the Edmonton Oilers.

July 2-6: Development Camp

After the dust settles on the draft and free agency, the Canadiens can begin to focus on the formation of their prospects by holding their annual development camp.

The camp includes any unsigned draft picks, any player in the entry-level system with fewer than 120 games played in the NHL total, but no more than 70 in the previous season, undrafted free agents, undrafted players, and any player who is not in the entry-level system but finished the preceding season disabled.

A player cannot take part in more than three such camps with a single team, so any players who have participated since the 2014 camp can no longer attend. This includes such prospects as Michael McCarron, Charles Hudon, Daniel Audette, Daniel Carr, Jacob de La Rose, Zachary Fucale, and Jeremy Gregoire.

It will be interesting to see if undrafted QMJHL scoring leader Tyler Boland gets a look. It’s also the only time that you will see any draft picks currently in the NCAA participate in NHL activity all season. This list includes Casey Staum, Nikolas Koberstein, Hayden Hawkey, and Jake Evans. We should also see Arvid Henriksson and Lukas Vejdemo come over from Europe.

July 5: Deadline for players to file for salary arbitration

This is final day for players to opt for salary arbitration. We listed the eligible players above. The arbitration schedule is then set by the League.

August 15: Last day to sign NCAA draft pick Colin Sullivan

Colin Sullivan has lingered on the Canadiens’ reserve list for six seasons now, and will finally go to unrestricted free agency on this date as it is highly unlikely that he will receive an entry-level contract from the Canadiens.

In general, all unsigned 2012 draft picks who played in the NCAA will go into unrestricted free agency at this point. Sullivan is a special case, being a 2011 draft pick, due to skipping an NCAA season while changing colleges.

Mid-September: Rookie Tournament

For the past two seasons, the Canadiens held a rookie tournament against the Toronto Maple Leafs, Ottawa Senators, and Pittsburgh Penguins at Budweiser Gardens in London, Ontario in place of a rookie training camp. There is nothing on the line, just three exhibition games against teams composed of players who are tryouts, unsigned draft picks, and first-year pros.

So far the Canadiens have not announced that they will participate in the tournament, so perhaps the format will change. For now the event remains in the calendar until further notice.

Two years ago Michael McNiven impressed so much during this tournament that he earned himself an Entry-Level Contract.

Listen to Andrew weekly on TSN 690 Radio Sundays at 8:05am on Habs Breakfast, part of Weekend Game Plan.