12 Most Valuable 1999 Upper Deck Baseball Cards
Looking back on the 1999 Upper Deck baseball set, it’s interesting to see just how much this set had going for it.
Whether you like the look and feel or not, clearly, Upper Deck was trying to push the envelope with the border design.
The grey, etched borders that tilted inwards just wasn’t something you usually saw.
Aesthetics aside, the 525-card checklist contained a ton of great players…
Future Hall-of-Famers like Ken Griffey Jr., Rickey Henderson, Tony Gwynn and more were always a welcome sight.
And there were so many solid rookies in this set.
Adrian Beltre and Roy Halladay ended up in Cooperstown.
But, other big-name players like Carlos Beltran, Eric Chavez, Aramis Ramirez, Troy Glaus, and A.J.
Burnett certainly lived up to the “Star Rookie” designation on their cards.
Overall, Upper Deck did a great job and ended their run in the 90s with a bang.
And in this guide, we’ll take a look at the 12 most valuable.
Let’s jump right in!
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Ross Uitts – Owner
- #1
1999 Upper Deck #205 Ken Griffey Jr.
PSA 10 Value $175Total PSA PopulationPSA 10 PopulationPSA 10 Grade Rate 0.0% (Set Avg: 0.0%)In the middle of the 1999 season, the Seattle Mariners and franchise legend Ken Griffey Jr. had the framework for a long-term contract extension.
The new deal would keep Griffey with the M’s for eight more years at $140 million.
It essentially guaranteed that Junior would play his entire career in the Pacific NorthweSt. However, Griffey wasn’t so sure.
The superstar center fielder had another fantastic year in ’99, notching an All-Star nod, Gold Glove, and Silver Slugger trifecta for the fourth consecutive year.
He slashed .285/.384/.576 with an AL-best 48 home runs, 123 runs, 91 walks, and 134 RBIs in 160 games.
Griffey was just as transcendent as ever.
Yet, his connection to the Mariners organization was starting to deteriorate.
He told the M’s that his desire to stay would hinge on the team’s performance and his feelings during the season’s last six weeks.
Seattle played middling ball from mid-August, finishing at 79-83, and Griffey was admittedly “miserable” the whole time.
By February 2000, the Mariners traded their franchise hero to his hometown Cincinnati Reds.
- #2
1999 Upper Deck #165 Rickey Henderson
PSA 10 Value $100Total PSA PopulationPSA 10 PopulationPSA 10 Grade Rate 0.0% (Set Avg: 0.0%)The 1998 season was a strange one for Rickey Henderson for several reasons.
For starters, it marked his fourth stint with the Oakland Athletics.
Secondly, at 39, Henderson shocked the baseball world by leading the Majors with 66 stolen bases.
Everyone knew he could still run and had plenty left in the tank, but nobody saw that coming.
He also led the American League in walks (118) for the first time since 1989, when he split time with Oakland and the New York Yankees.
The walks, by themselves, weren’t all that strange.
It was that he struck out nearly as many times.
In 542 at-bats, Henderson struck out 114 times, the only time he’d ever surpassed 100 strikeouts in a season and easily the worst mark of his career.
Sure, the 542 at-bats were much more than he’d had in quite some time, giving him more chances than usual to strike out.
But even during the 80s, when he got a similar number of at-bats, he was striking out somewhere between 60-90 times.
It didn’t matter really.
Rickey was still producing at a high level.
Despite his production, though, it would be his last time in Oakland green and yellow as he would be headed to the East Coast in 1999.
Soon after Series One was released in December 1998, Rickey would sign with the New York Mets, landing another card in Series Two.
- #3
1999 Upper Deck #426 Rickey Henderson
PSA 10 Value $100Total PSA PopulationPSA 10 PopulationPSA 10 Grade Rate 0.0% (Set Avg: 0.0%)The New York Mets didn’t care that Rickey Henderson was about to turn forty.
They knew they needed a leadoff hitter, so they went all-in with the greatest one to play the game.
“He was one of the most dominating players I managed against,” Mets manager Bobby Valentine said.
“He might have lost a step, but he still has the ability to disrupt minds, as well as defenses.” Unable to get the contract he wanted back home in Oakland, Henderson signed a one-year, $2.3 million deal with the Mets for the ’99 season (with an option for year two.) His numbers had fallen off a cliff over the past half-decade, but Henderson at 50% seemed much better than the sub-replacement level leadoff options New York trotted out in ’98.
Remarkably, the Mets got more of Rickey than they paid for.
The all-time steals leader earned the Sporting News Comeback Player of the Year Award, slashing .315/.423/.466 with 12 homers and 37 steals in 121 games.
With their leadoff star at his best in years, the 97-win Mets snatched the NL Wild Card for their first playoff appearance since 1988.
- #4
1999 Upper Deck #474 Tony Gwynn
PSA 10 Value $100Total PSA PopulationPSA 10 PopulationPSA 10 Grade Rate 0.0% (Set Avg: 0.0%)Nearly eighteen years and eight batting titles into his extraordinary Hall-of-Fame career, San Diego Padres right fielder Tony Gwynn had earned his place as the greatest pure hitter of the 1980s and 1990s.
August 6th, 1999, was the moment it all seemed to snap into focus.
One day before, Gwynn had slapped four hits to close within one knock of joining the immortal 3,000 Hit Club.
He didn’t let the suspense carry on long, dunking a first-inning single off Expos rookie Dan Smith to seal the deal.
“The relief that you feel is the first thing that hits you,” Gwynn said.
“And then I started to feel emotional and then all these guys started coming over to me.
When I got back to the dugout, I could not sit down.” Only one MLB hitter (Wade Boggs) has reached 3,000 in fewer at-bats.
And only one other player has done it in fewer games (Roberto Clemente).
Gwynn’s consistent excellence was often taken for granted, but there is no denying how singular his hitting acumen was.
The 39-year-old ended his history-making campaign with a .338 average in 111 games.
It would have been good enough for second in the NL if the injury-struck legend had qualified for the league batting title.
- #5
1999 Upper Deck #2 Adrian Beltre Star Rookie
PSA 10 Value $75Total PSA PopulationPSA 10 PopulationPSA 10 Grade Rate 0.0% (Set Avg: 0.0%)The 1999 season was one of controversy and progress for Los Angeles Dodgers third baseman Adrian Beltre.
On the field, the sophomore slugger improved leaps and bounds from his spotty rookie year, slashing .275/.352/.428 with 15 home runs, 27 doubles, five triples, 18 stolen bases, 84 runs, and 67 RBIs.
Off the field, things were much more complicated.
During the Dodgers’ Spring Training stay in Arizona, Beltre revealed to agent Scott Boras that he was actually nineteen instead of his listed age of twenty.
This meant that the Dominican Republic native had been signed by the organization at fifteen, not sixteen, a no-no under Major League Baseball policy.
The practice of fudging Dominican prospects’ ages for signing purposes is familiar, and it often costs players tens, if not hundreds, of thousands of dollars on a year-by-year pay scale.
Boras wanted Beltre to be ruled a free agent to recoup lost earning potential on the open market.
Commissioner Bud Selig ultimately ruled against it.
Instead, he awarded Beltre the difference between his signing bonus and the $48,000 he would have made a year later.
Selig also suspended two Dodgers scouts and the organization’s Dominican baseball presence for a year.
- #6
1999 Upper Deck #269 Roy Halladay Star Rookie
PSA 10 Value $75Total PSA PopulationPSA 10 PopulationPSA 10 Grade Rate 0.0% (Set Avg: 0.0%)Roy Halladay used brute force to make his rookie season mostly successful, even if it was a harbinger of trouble to come.
The 22-year-old right-hander made the Toronto Blue Jays out of camp in 1999 thanks to his dynamite stuff and raw talent.
Halladay used a steady, overwhelming diet of high fastballs to overwhelm hitters, and it worked like a charm for most of his debut year.
He appeared in 36 games as a situational reliever and starting pitcher, pitching to a 3.92 ERA in 149.1 innings.
Halladay would have finished seventh if he had qualified for the AL ERA title.
It all looked great on paper, yet there were definitely some issues.
Halladay had plenty of fireworks in his arm.
However, his lack of control and movement led to a boatload of walks (82).
Those free passes raised his WHIP to an unsightly 1.574.
One year later, the former first-rounder’s command issues earned him a humiliating demotion all the way down to Single-A.
- #7
1999 Upper Deck #49 Cal Ripken Jr.
PSA 10 Value $50Total PSA PopulationPSA 10 PopulationPSA 10 Grade Rate 0.0% (Set Avg: 0.0%)The streak was over, and Cal Ripken’s body got the memo.
After taking himself out of the lineup for what would have been consecutive game #2,633 in September 1998, the 38-year-old Baltimore Orioles third baseman was tapped.
Ripken missed 76 games at the beginning and end of the season with nagging back issues.
The O’s legend played with a bum back for much of the end of his streak, and it zapped his overall productivity at the plate.
In 1999, Ripken listened to his body and took a conservative approach to his health for the first time in a long time.
It made sense to do so with the Orioles languishing in the mediocre middle of the MLB standings.
Ripken’s numbers reflected the needed reSt. With a heavy heart over the March 25th passing of his father, Cal Ripken Sr., Junior set new career highs in batting average (.340), slugging percentage (.584), and OPS (.952).
The future Hall-of-Famer also hammered 18 home runs in 332 at-bats after hitting just 14 in 601 at-bats the year before.
- #8
1999 Upper Deck #154 Derek Jeter
PSA 10 Value $50Total PSA PopulationPSA 10 PopulationPSA 10 Grade Rate 0.0% (Set Avg: 0.0%)In a career full of sparkling regular seasons and clutch October/November performances, Derek Jeter’s 1999 campaign was his pinnacle.
The 25-year-old shortstop set career bests in home runs (24), hits (an MLB-best 219), triples (9), walks (91), OBP (.438), slugging percentage (.552), OPS (.989), and RBIs (102), the latter marking the only 100 RBI season of his two-decade career.
If not for the inflated video-game numbers of the Steroid Era, Jeter would likely have won the AL MVP going away.
His defense was iffy, but his impact on the 98-win Yankees juggernaut would have made him the prohibitive favorite in the current baseball landscape.
Jeter settled for sixth.
However, the real validation for the future Captain’s efforts had nothing to do with baseball writers’ votes.
Jeter hit .375 with a .976 OPS and ten runs scored in twelve postseason games as New York ripped an 11-1 hole through the field to repeat as World Series champions.
It was the Yankee’s third title in four years.
- #9
1999 Upper Deck #287 Carlos Beltran Star Rookie
PSA 10 Value $40Total PSA PopulationPSA 10 PopulationPSA 10 Grade Rate 0.0% (Set Avg: 0.0%)The Kansas City Royals were terrible once again in 1999, missing the playoffs for the 13th consecutive season with a record of 64-97.
It wasn’t all lost, though.
The Royals struck gold during a grey season with switch-hitting rookie standout Carlos Beltran.
The 22-year-old former second-round pick was one of the lone highlights of Kansas City’s offense, hitting .293 with 22 home runs, 112 runs, 108 RBIs, and 27 stolen bases in 156 games.
He became the first rookie since Fred Lynn (1975) to tally at least 100 runs and 100 RBIs, and just the eighth overall.
The Puerto Rican native was still quite raw, as evidenced by his 123 strikeouts in 663 at-bats.
Regardless, he was a godsend on a minimum $200,000 contract for a Royals franchise running out a paltry $16.6 million payroll.
Beltran was the no-brainer choice for AL Rookie-of-the-Year, snagging 26 of 28 first-place votes.
He took the news in stride, choosing to focus on the work to do rather than his first-year accomplishments.
“I’m sure Carlos, in his mentality, doesn’t even understand the impact,” Royals manager Tony Muser said.
- #10
1999 Upper Deck #158 Mariano Rivera
PSA 10 Value $30Total PSA PopulationPSA 10 PopulationPSA 10 Grade Rate 0.0% (Set Avg: 0.0%)1999 is the perfect evidence for Mariano Rivera’s claim as the greatest closer in MLB history.
The New York Yankees righty was the final boss for the team’s dynasty-cementing World Series run, posting a 1.85 ERA, 0.884 WHIP, and an MLB-leading 45 saves in 66 appearances.
Rivera surrendered just 43 hits and 18 walks in 69.0 innings.
When former teammate Jorge Posada later remarked, “How ridiculous this guy was going through people,” 1999 may very well have been what he was talking about.
Rivera did not give an earned run from July 21st through the playoffs, tallying 20 saves in 28 games while holding opponents to a minuscule .136 average.
The crescendo came in the World Series when the 29-year-old blew the doors off the Atlanta Braves in a four-game sweep.
Rivera logged 4.2 scoreless innings and two saves in three appearances to become the fifth reliever to win World Series MVP.
And to top it off in the way only legends do, the first-ballot Hall-of-Famer broke slugger Ryan Klesko’s bat on three consecutive pitches.
Just like a final boss would.
- #11
1999 Upper Deck #328 Pedro Martinez
PSA 10 Value $30Total PSA PopulationPSA 10 PopulationPSA 10 Grade Rate 0.0% (Set Avg: 0.0%)Pedro Martinez was the exception in an era where offense reigned, and pitching was a thankless job.
The Boston Red Sox hurler didn’t sweat hulking hitters, (allegedly) juiced balls, and a game tailored for high-scoring slugfests.
Martinez was a freak of nature with a patently unfair fastball/changeup combo.
His deceptive arm slot and release on both pitches were a pure antidote to the high-scoring offense of the day.
Martinez was at the height of his considerable powers in 1999.
The 27-year-old Dominican Republic native paced the American League in nearly every major pitching category, including wins (23) and WHIP (0.923).
His league-leading 2.07 ERA was a remarkable 137 points lower than second-place finisher David Cone.
Martinez’s AL-best 313 strikeouts set a new Red Sox franchise record, and his 243 ERA+ remains the fifth-best mark of the post-strike era.
(1995-present).
It was an exercise in utter dominance and an easy recipe for a second Cy Young.
Martinez’s unanimous award triumph made him and 1999 NL Cy Young winner Randy Johnson the second and third pitchers in MLB history to secure the honor in both leagues.
- #12
1999 Upper Deck #337 Frank Thomas
PSA 10 Value $30Total PSA PopulationPSA 10 PopulationPSA 10 Grade Rate 0.0% (Set Avg: 0.0%)When is a .300 season with a .400-plus on-base percentage not enough.
It’s not often, but that was the case for Chicago White Sox slugger Frank Thomas during the 1999 season.
The 31-year-old Big Hurt was in a precarious spot with the retooling White Sox organization.
Chicago’s lineup was utterly ripped apart by the departures of Robin Ventura and Albert Belle to free agency, and Thomas was left to sulk in the wreckage.
What’s worse, the future Hall-of-Famer’s relationship with manager Jerry Manuel was on the outs.
Manuel and Thomas bickered all season long over whether or not Thomas should play in the field.
Manuel wanted to slot Thomas in at first, at least part-time, while the slugger wished to serve as a DH only.
“Frank doesn’t think he’s adequate out there,” Manuel told the media.
“He doesn’t want to be embarrassed in public.” It was all a headache, and Thomas’ injuries only exacerbated things.
The “Big Hurt” hit just 15 home runs in 590 plate appearances, his worst full-season output thus far.
Even his .305 batting average and 414 on-base percentage weren’t enough to keep the critics from chirping.
Ross’s Take
While it may be a bit overlooked in today’s market, I think this set offers plenty of reason to take a second look.
If nothing else, the inserts (which we’ll get to later) were great.
Still, the base set offers an awesome balance of design, big-name stars, and solid rookies.
Interestingly, you’ll notice that the checklist runs to #535 even though it only contains 525 cards.
For some reason, ten cards were left out of the set, and it is believed they were all part of a certain subset that Upper Deck decided to omit.
Speaking of subsets, there were multiple in the checklist, including: Star Rookies (#1 – 18; 266 – 292) Foreign Focus (#229 – 246) Checklists (#247 – 255; 527 – 535) Arms Race ’99 (#518 – 526) Upper Deck hit a home run with the inserts in this set, including oversized reprints of Ken Griffey Jr.’s previous UD cards, foil-stamped and numbered “jumbo” reprints of his ’89 rookie, and several different autographed and game-used cards.
It was a heck of a way to promote and celebrate their tenth anniversary in the hobby.
So, even if the base set doesn’t motivate you all that much, these inserts offer plenty of reasons to open packs still today.
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