Instead, Boston hit an unwanted milestone by surrendering a third-period lead and suffering its first regulation loss after leading through two periods, as well as its first regulation setback after scoring first.
The Bruins, leading by one entering the final 20 minutes, were felled by goals from Ryan McLeod (6:08) and Darnell Nurse (15:11) in the eventual 3-2 loss, which snapped Boston's 10-game winning streak.
"I thought we checked pretty good tonight, but I thought the Oilers were the better team," said Montgomery. "They were good, we weren't good enough. I thought they outplayed us, outworked us, and out-coached us."
Boston had been 33-0-3 when scoring first and were set to become just the third team in NHL history with such a stretch of 37-plus games at any point of a season (1977-78 Montreal Canadiens, 39-0-4; 1971-72 Bruins, 35-0-6). The Bruins had also been 35-0-2 when leading after two periods.
The Bruins, who are now 49-9-5 this season, lost for just the third time in regulation on home ice (26-3-3).
"It's in the third where we got back on our heels and didn't play our game and they took it to us," said Bruins captain Patrice Bergeron. "I thought the first 40 wasn't perfect, but we still had some good control of the game and we're up by one and I think that's where we've had success all year. Obviously, we're not happy with that third, but we've got to learn from that. I thought we got on our heels and we didn't deny their speed and they took it to us."
Despite being up, 2-0, after the first period on tallies from Brad Marchand (3:51) and David Pastrnak (with 0.3 seconds to go in the frame), Montgomery did not believe the Bruins had played to their standard.
"I mean, after the first period we said that we were lucky to be up 2-0," said Montgomery. "They were the better team…I thought we got better in the second. I thought that we were good in the second, we passed up too many opportunities to push the lead. We were a very non-competitive team offensively tonight, I guess is the best way to say it."
Boston's bench boss was not pleased with his club's lack of assertiveness when it came to putting shots on Edmonton netminder Stuart Skinner.
"Turning down shots, not driving to hard areas, not winning enough battles to create O-zone time," said Montgomery. "So, it was a good lesson for us to learn because they played well…we sat back at times, where we should've been pushing the envelope, we were sealing the envelope."