Ralph Backstrom and Jean Beliveau each had two goals apiece in a 9–1 Montreal win at the Montreal Forum on October 23. Rudy Pilous, coach of the Black Hawks, was far from pleased with his team's performance and fined his team $100 for the poor performance.
Beliveau had the hat trick November 29 as Montreal beat Detroit 6–2 at the Forum. Gordie Howe was injured in a collision with Doug Harvey near the end of the first period and was taken to hospital. There was no serious damage and Howe was given an ovation when he returned in the third period. The next night, Montreal sneeringly pasted the Red Wings 7–0 as Jacques Plante got his third shutout of the season.
On January 3, Harvey was back in the Canadiens lineup and scored two goals in a 5–1 win over the New York Rangers at the Forum. A crowd of 14,711 saw a free-for-all at the end of the game. In the last minute of play, Plante got two penalties, one of them a major that sparked the fight. Jimmy Bartlett had skated right into Plante, and Plante retaliated by punching Bartlett. In no time at all, every player on the ice was involved except Rangers' net minder Gump Worsley, who decided to have none of the nonsense. Referee Dalton McArthur gave Bartlett a double major, one for charging and one for fighting, and a misconduct penalty. Harvey and Lou Fontinato also received major penalties.
On February 1, the Rangers downed the Red Wings 5–4 at Madison Square Garden. Lou Fontinato became incensed when Gordie Howe whacked Eddie Shack over the ear with his stick, and challenged the right wing. Howe terminated the fight with an uppercut that broke Fontinato's nose and left it several degrees off centre. On February 5, the Rangers beat the Wings 5–0 on Worsley's shutout. Detroit coach Sid Abel, formerly Howe's centreman, was furious at his team and fined 14 players $100 each for playing what he described as "the worst game of hockey he had seen in 20 years".
On February 15 at Madison Square Garden, the Gumper had Montreal shut out with ten minutes remaining. Then the Canadiens scored 5 goals to win 5–1. Coach Phil Watson was red-faced and screaming at his Ranger players and ordered every player except Worsley out on the ice for an after-game workout. Watson said Worsley hadn't played so bad. General manager Muzz Patrick said the workout was in lieu of fines.
With five games left in the season, the Rangers had a seven-point lead over Toronto. Then the Rangers went into a fatal tailspin, and the Leafs got hot. The key game was played March 19 between Toronto and the Canadiens. Plante couldn't play due to a severe case of boils, and so the Canadiens used Claude Pronovost in goal. He was bombed for five goals before coach Toe Blake yanked him in the third period. He was replaced by another nobody, Claude Cyr. It was his first and last NHL game. He gave up only one goal the rest of the way, but the damage was done. Toronto won 6–3. The Canadiens brought up the more capable Charlie Hodge from the Montreal Royals and on March 22, he beat the Rangers 4–2. The Rangers still had a chance to make the playoffs if Detroit beat Toronto. The Red Wings had a 3–0 lead that collapsed, and the Leafs won 6–4 and ousted the Rangers, making the playoffs themselves.
The Montreal Canadiens again won the regular season standings and again their players dominated the All-Star nominations (with six of a possible twelve, the same number as in 1956) and trophies as Jacques Plante won his fourth straight Vezina Trophy, Tom Johnson won the James Norris Memorial Trophy, ending teammate Doug Harvey's four-year monopoly, and Dickie Moore won the Art Ross Trophy, setting a new record for total points in a season: with a 41-goal, 55-assist campaign, "Digger" broke "Mr. Hockey's" record by a single point.
This season marked the final time until 1967 where we would see an active player that had played for a team not in the Original Six. Former Brooklyn Americans player Ken Mosdell suited up for 2 postseason games for the Canadiens that year, and retired after Montreal won the Cup.
The following is a list of players of note who played their first NHL game in 1958–59 (listed with their first team, asterisk(*) marks debut in playoffs):
Coleman, Charles L. (1976), Trail of the Stanley Cup, Vol III, Sherbrooke, QC: Progressive Publications
Diamond, Dan, ed. (1994). Years of glory, 1942–1967: the National Hockey League's official book of the six-team era. Toronto, ON: McClelland and Stewart. ISBN0-7710-2817-2. {{cite book}}: Invalid |ref=harv (help)
Diamond, Dan, ed. (2000). Total Hockey. Kingston, NY: Total Sports. ISBN1-892129-85-X. {{cite book}}: Invalid |ref=harv (help)
Dinger, Ralph, ed. (2011). The National Hockey League Official Guide & Record Book 2012. Toronto, ON: Dan Diamond & Associates. ISBN978-1-894801-22-5.{{cite book}}: CS1 maint: ref duplicates default (link)
Dryden, Steve, ed. (2000). Century of hockey. Toronto, ON: McClelland & Stewart Ltd. ISBN0-7710-4179-9.{{cite book}}: CS1 maint: ref duplicates default (link)
Duplacey, James (2008), Hockey’s Book of Firsts, North Dighton, MA: JG Press, ISBN978-1-57215-037-9
Fischler, Stan; Fischler, Shirley; Hughes, Morgan; Romain, Joseph; Duplacey, James (2003). The Hockey Chronicle: Year-by-Year History of the National Hockey League. Lincolnwood, IL: Publications International Inc. ISBN0-7853-9624-1.
McFarlane, Brian (1969), 50 Years Of Hockey, Winnipeg, MAN: Greywood Publishing, ASINB000GW45S0
McFarlane, Brian (1973). The Story of the National Hockey League. New York, NY: Pagurian Press. ISBN0-684-13424-1. {{cite book}}: Invalid |ref=harv (help)