Best time for "Match the Dealer" bet = Never
I did calculations on this and other side bets awhile back, and although I don't remember the house edge on this specific bet, most side bets carry a 3-7% house edge. I also recall that the true count (using HiLo) has to be around >+12 or <-12 before the player has an advantage with the "Match the Dealer" bet. Counts like this are extremely rare, and practically speaking, you'd never want to play this side bet.
In addition to Lucky Ladies and O/U 13, I'm only aware of two other side bets which might be beatable:
1) Royal Match - Pays when the player's two cards are suited. Premium payout comes with a KQ suited. This might be beatable when the remaining deck has a very uneven distribution of each of the four suits.
2) Big Slick - I think there is a payout if your first two cards make a 2-card straight, or if your first two cards are a pair. The premium payout for this game is AK suited (or, "big slick"). I think the player has an advantage in this game if there is a significantly higher than normal distribution of aces and kings in the remaining pack. The game may be beatable if you side count aces and kings.