Now, Tim Thomas, the former University of Vermont star, is hoping to add his name to that elite list. To do so, he will have to win one more game in the 2010-11 season -- Wednesday's Game 7 in Vancouver.
Ken Dryden, Ed Belfour, and Mike Richter have already accomplished this rare feat.
Thomas, a Michigan native, and the Ontario native Dryden might deserve an asterisk beside their names in NCAA lore, given they fulfilled the benchmark definition of "student athlete."
Both graduated before going pro.
Belfour, a Manitoba native, led his Dallas Stars to Stanley Cup history with the 1999 victory against Buffalo. He was 12 years removed from his one season spent at the University of North Dakota in 1987.
The American-born Richter paralleled Belfour's college career -- two seasons at the University of Wisconsin from 1985-87 --- en route to the New York Rangers' Cup parade in 1994.
There have been others that have come close.
Providence College star Chris Terreri's name is etched on the Stanley Cup after backing up Marty Brodeur with New Jersey's Cup wins in 1995 and 2000; and Dwayne Roloson, an All-American at U-Mass Lowell, led the Edmonton Oilers to the 2006 Final before ending his run with an injury in Game 1. The Oilers lost to Carolina in seven games.
And standout Blackhawk netminder, Tony Esposito – who also graduated on time -- led his Hawks to the 1971 Final against Dryden's Canadiens. Montreal prevailed in seven games.
Thomas stands alone as the only Final starting goaltender in Stanley Cup history to play four years at the varsity level in college.
"It's an honor to be mentioned in the same sentence as Ken Dryden," said Thomas. "He played in the same league (ECAC) I played college hockey."
Dryden played three years at Cornell from 1966-1969, when NCAA rules allowed only three years of varsity eligibility, like Esposito at Michigan Tech.
After red-shirting his freshman year in 1965-66, Dryden won the national championship his first year of varsity play in '67. He then lost the 1969 title game before graduating a few months later.
Esposito also won a national title his sophomore year in 1965.
In his first season with the Canadiens in 1970-71, Dryden began a goaltending run unlikely to be matched in future NHL history by a player of any roots -- six Cups in nine years, including a Conn Smythe Trophy that rookie year.
Thomas, meanwhile, led his Catamounts to the 1996 Frozen Four his junior season, losing to Colorado College in the semifinal in overtime.
If Thomas' stars are aligned and his Bruins win the Cup on Wednesday night, he will be the clear favorite to win the Conn Smythe Trophy as the Most Valuable Player of the playoffs, putting him in exclusive company with Dryden as the only former NCAA player to win a Cup and a Conn Smythe.
Favored also to win the Vezina Trophy as the League's best goaltender in the regular season, Thomas has a chance to claim the Stanley Cup, the Conn Smythe and the Vezina. No NCAA player has ever done that.
While Thomas' career playoff tally of 42 games thus far significantly trails Richter's 76, Belfour's 161 and Dryden's 112 games totals, Thomas has a 2.11 career playoff goals-against average into Game 6, compared with Belfour's 2.17, Dryden's 2.40, and Richter's 2.68 lifetime marks.
Thomas' 2011 overall 2.07 GAA into Game 7 – in which he allowed but two Canucks' goals in the 5-2 win -- matched Richter's exact total in 1994, but lags considerably behind Belfour's and Dryden's amazing 1.67 and 1.55 mark, respectively, in their 1999 and 1977 Cup-winning seasons.
But his stellar 1.33 GAA these past six Final games should bring considerable attention to being named the Conn Smythe winner – even if Vancouver wins -- a first since Anaheim's J.S. Giguere in 2003, when his Ducks lost to the Devils. Giguere went 15-6 with a 1.62 GAA that postseason.
Thomas also set a new regular-season save-percentage mark of .938, eclipsing Dominik Hasek's .937.
Esposito played 99 playoff games with a 3.07 GAA; Miller and Turco have 47 games each with a 2.47 and 2.17 mark, respectively.
Dryden was just beyond age 20 when his NHL career took off; Thomas beyond 30 before his NHL career gained momentum.
Now three years shy of turning 40, Thomas is one victory away from reaching the NHL's highest peak.
"Anybody that knows the story of Tim Thomas, he's taken a real bumpy road to get to the NHL," Bruins coach Claude Julien said last week. "He's had so many obstacles in front of him that he's overcome, it makes him a battler. It makes him the perfect goaltender for our organization because that's what we are. We're a blue-collar team that goes out and works hard and earns every inch of the ice that you can get."
Indeed, that road was long with many a winding turn for Tim Thomas from Flint, Mich., to Burlington, Vermont, to Causeway Street in Boston -- to a possible downtown parade this weekend.
For most of the front end of his career, he was that proverbial diamond in the rough.
Thomas would endure the best and worst of minor-league experiences. He enjoyed a championship run in Finland before finally latching on in the NHL with the Bruins organization.
"I had never even been to Vermont -- or even east of Buffalo," Thomas once told NHL.com in an exclusive interview. "I just wanted to go and become the first person in my family to graduate. To be completely honest, I'm sure I was hoping to someday play in the NHL, but my ultimate goal was to get the scholarship and play college hockey."
He was 28 when that "someday" finally came in his NHL debut. He did not become a regular with the Bruins until he was past 30.
Thomas has played every minute of the 24 playoff games since April that includes three shutouts and 15 wins.
Sixteen, however, is the ultimate goal in the Stanley Cup Playoffs.
Thomas has so many supporters hoping he wins the Cup, but one truly stands out. Martin St. Louis, who won the Cup with Tampa Bay in 2004, is firmly on the bandwagon after the Bruins knocked his team out last round. Thomas and S t. Louis went to Vermont together.
"I hope he wins the Cup," said a dejected St. Louis right after his former teammate all four years at Vermont stoned the Lightning, 1-0, in Game 7 of the Eastern Conference Finals. "I really do. Timmy's had a long road to get here."
He and his Bruins are now looking up at just one NHL team; the ceiling now less fragile and within immediate reach.
"When I was in college, I remember looking at what [Dryden] accomplished and his stats and I was actually gunning to reach his," Thomas said earlier this week. "I'd like to hope that I can finish it off and win the Cup like he did."