BOSTON — The Toronto Maple Leafs could find themselves in a tricky roster situation as October turns to November.

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Defenseman Jani Hakanpaa and forward Connor Dewar have joined the team for their two-game road trip through Boston and Winnipeg, a sign that both players could be nearing a return when they are permitted to do so under long-term injured reserve (LTIR) conditions.

"I thought it was good for them to come and be around the players and the team and getting on the ice with the guys a little bit here now," Maple Leafs head coach Craig Berube said of both players. "So they're getting to the point where it's getting close."

Hakanpaa (knee) and Dewar (shoulder) were placed on LTIR at the start of the season. This made them ineligible to return to the active roster until they missed a combination of 10 games and 24 days. Since Toronto’s first 24 days include 11 games, the earliest return date for both players is Nov. 2, against the St. Louis Blues.

Related: Maple Leafs Finally Sign Jani Hakanpaa to One-Year Deal Following Summer of Uncertainty

Both players have been regular participants at practice since they were placed on LTIR to start the season. Once both players are cleared to return, the team will need to make some roster adjustments.

Puckpedia.com reports the Leafs have $1.18 million in salary cap space, exactly matching Dewar's cap hit. While Dewar could be activated immediately on Nov. 1, the team would need to clear space by waiving someone before sending them down. However, if a short-term injury occurs, Dewar could be added to the 23-man roster without any corresponding roster move.

Hakanpaa’s $1.47 million cap hit presents a greater challenge if Toronto aims to activate both players. This would require removing two players from the active roster while accounting for their cap hits.

Related: 'It Just Had To Get Taken Care Of': Connor Dewar Reveals Reason Behind Shoulder Surgery Following First Full Practice with Maple Leafs

Waiving someone like Myers and sending him to the Marlies could create room for one player, but additional roster space would still be needed for Hakanpaa.

Another option to clear roster space is defenseman Timothy Liljegren, who has only played one game this season since signing a two-year, $6 million extension this summer.

"I mean, right now it's a little bit of a numbers game. I know I threw him in there for a game. And it’s hard with one game. I mean, he's got to be patient right now," explained coach Berube following the club's morning skate in Boston on Saturday. "That's just the way it is. We make decisions as a staff in an organization of what we feel is best at the time. So he's working on his game. He's working. And, you know, he'll get another opportunity."

Liljegren’s future has been under speculation since the season began, and he seems to be on the roster bubble. If the Leafs' roster stays healthy over the next three games, they might struggle to activate both players, which could mean further moves or require one of them to wait.