The teams last met a decade before in the 1958 Stanley Cup Finals where Montreal prevailed 4 games to 2. The 1968 series was characterized by Montreal taking advantage of chances and then playing excellent defensive hockey to hold leads. Canadiens veteran Gump Worsley outplayed Gerry Cheevers, particularly in Game 3. Bobby Orr was still recovering from the first surgery on his left knee, made few rushes and notched only two assists in the series.
Game 1 at the Montreal Forum was a very rough game where the teams tried to establish a physical edge. The teams' tough men, Boston's Ted Green and Montreal's John Ferguson fought in the first period while rookies Derek Sanderson and Danny Grant fought in the second period. Ken Hodge opening the scoring with his first career playoff goal, equalized by Henri Richard in the first period. Montreal pressed and outshot Boston 35-22 and Claude Provost netted the winner at 14:40 of the third period for a 2-1 Canadiens win.
Game 2 at Montreal was a tamer affair but the Canadiens once again outshot and out chanced the Bruins. In the first period, Jacques Lemaire opened the scoring with his first career playoff goal but Ken Hodge responded. In the second period, Jacques Laperriere scored and then Lemaire's second of the game staked Montreal to a 3-1 lead. With Jean Béliveau and Claude Provost both in the penalty box, Ted Green potted his first career playoff goal on the 5 on 3 Power play to cut the lead to 3-2. In the third period, Dick Duff and John McKenzie traded goals 23 seconds apart. The Bruins fought to tie up the game but Beliveau sealed the Canadiens 5-3 win.
Game 3 at the Boston Garden saw the Bruins out chance the Canadiens, particularly in the first ten minutes of the game. Ed Westfall opened the scoring and Gump Worsley made several excellent saves, particularly on Tom Williams. Jean Beliveau tipped in a Jacques Laperriere shot on the power play to tie the game 1-1. Derek Sanderson took undisciplined penalties at the end of the first period and at 6:50 of the second period which took the pressure off Montreal. On the power play, Claude Provost beat Cheevers with a long, unscreened shot that demoralized the Bruins. After that, the defensemen overcompensated and tried to block all Montreal's shots instead of checking. Dallas Smith failed to block a Ralph Backstrom shot which slide past Cheevers and later in the period, the Bruins were out-manned in front of their net and John Ferguson tapped in a goal mouth pass to make it 4-1. A Tom Williams spinning shot beat Worsley with five seconds left in the second period to make it 4-2. The Bruins pressed in the third period but Worsley was excellent, stopping Williams on a breakaway. Ted Green hit the post on a slap shot from the point and then Dick Duff scored to make it 5-2. The Bruins had few chances after Duff's goal and Montreal took a 3-0 series lead.
Game 4 at Boston was the only game of the series that the Bruins outshot the Canadiens. After a scoreless first period, Ed Westfall opened the scoring 49 seconds into the second period. Claude Larose then took over the game, evening the score at 12:58 of the second period and staking Montreal to a 2-1 lead at 7:20 of the third. He then set up Ralph Backstrom with less than four minutes to play in the game. Ken Hodge made it 3-2 with 1:26 left to play but Montreal hung on to sweep the Bruins in four games.
This was the first Stanley Cup after the 1967 expansion. Montreal defeated Boston and Chicago to advance to the finals as the East Division champion. St. Louis would defeat Philadelphia and Minnesota to advance to the finals as the West Division champion.