2. December 12, 2023: at Boston Celtics
This is a big game for a lot of the same reasons the Nuggets matchup is, but it hits a lot closer to home in the Eastern Conference.
Despite disappointing in last year's playoffs, Boston comes into the season as the betting favorite to win the Eastern Conference in the 2023-24 season.
If the Cavaliers want to mark a dark horse run to the finals as a surprise Eastern Conference winner, there's a good chance that road goes through Boston.
We went 3-1 against the Celtics last year, with all three of those wins coming in overtime. It's clear this team isn't afraid of Boston, and that attitude can pay dividends in the postseason.
The Cavs will just want to make sure they're building momentum for an eventual playoff matchup by getting the best of the regular season series too, and the first opportunity to do that will be in a very tricky road matchup in December.