15 Most Valuable 1999 Topps Baseball Cards

Most Valuable 1999 Topps Baseball Cards


After a historic 1998 MLB season that saw Mark McGwire and Sammy Sosa hit 70 and 66 home runs, the 1999 Topps baseball card set focused on celebrating.

So, Topps dedicated card #220 in Series One packs to McGwire's 70 home runs and card #461 in Series Two packs to Sosa's 66 home runs.

Moreover, there were 70 variations of #220 and 66 variations of #461...

That's right: Topps created a unique card for each one of the legendary sluggers' home runs from the 1998 campaign.

Those cards immediately grabbed collectors' attention, but there are plenty more stars and Hall of Famers to be found inside the 462-card checklist.

And in this guide, we'll take a look at the 15 most valuable.

Let's jump right in!

Ross Uitts

Ross Uitts - Owner

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Let's be clear: most of the cards from this set do not have any value these days.

Like the 1999 Bowman and Upper Deck sets, print runs were large enough and print quality was good enough that there is generally enough supply to meet demand.

So, for the cards on this list to be worth much, they'll have to be graded by PSA to be in perfect, gem mint condition.

That means the card needs to be flawless.

Now that we got that out of the way, let's take a look at the list:

1999 Topps #85 Derek Jeter

Estimated PSA 10 Gem Mint Value: $65

One of the last great dynasties of the modern era, the turn-of-the-millennium New York Yankees were nothing short of a juggernaut.

The 1999 season saw the Bombers at the peak of their powers.

After manager Joe Torre's early-season fight with cancer and subsequent remission, the Yankees locked in and propelled forward in their pursuit of a second straight World Series championship.

Leading the charge was 25-year-old shortstop Derek Jeter.

In the best season of his two-decade Hall-of-Fame career, Jeter posted career highs in batting average (.349), OBP (.438), slugging percentage (.552), OPS+ (153), hits (an MLB-best 219), runs scored (134), walks (91), home runs (24), and RBIs (102), among other categories.

It wasn't just a great season for the sixth-place AL MVP finisher and two-time All-Star.

It was one of the best all-around single-season performances for a shortstop in modern baseball history.

The future Yankees captain ramped up the heroics in October, leading New York to another World Series triumph.

Jeter hit .455 in an ALDS sweep of the Texas Rangers, .350 in a five-game ALCS win over the hated Boston Red Sox, and .353 in a four-game Fall Classic sweep of San Diego.

The Yankees added yet another trophy to the case, and Jeter was far from done bringing hardware home to the Bronx.

1999 Topps #85 Derek Jeter Baseball Card

1999 Topps #100 Ken Griffey Jr.

Estimated PSA 10 Gem Mint Value: $65

In his final year as a Seattle Mariner, everything seemed to be changing around future Hall of Fame center fielder Ken Griffey Jr.

For one, the Mariners moved out of the homer-happy Kingdome in favor of a brand-new, more pitcher-friendly stadium.

Many pundits questioned whether Griffey would be happy at Safeco Field or would prefer to go elsewhere in free agency at the season's end.

It just felt different in the Pacific Northwest.

Randy Johnson was dealt to Houston the year before, leaving a giant hole at the top of the rotation.

And as other players left or got hurt, the 79-win Mariners seemed to be retooling and looking toward the future.

That future wouldn't include Griffey, as he packed up and left for Cincinnati in the offseason.

However, he'd give Seattle one last parting gift to wrap his first run with the M's in the form of yet another stellar All-Star campaign.

In 606 at-bats, Griffey Jr. posted a .285/.384/.576 slash line with an AL-best 48 home runs, 123 runs scored, 134 RBIs, 26 doubles, and 24 stolen bases.

Finishing tenth in the AL's MVP race, Griffey earned his tenth straight All-Star appearance, tenth straight Gold Glove, fourth straight Silver Slugger, and second straight Home Run Derby title to wrap up eleven years of pure excellence in Seattle.

1999 Topps #100 Ken Griffey Jr. Baseball Card

1999 Topps #220 Mark McGwire HR Record

Estimated PSA 10 Gem Mint Value: $50

How does one orchestrate a worthy encore to one of the most iconic seasons in MLB history?

After chasing down and passing Roger Maris for the all-time home run record (alongside Sammy Sosa), that's the question that St. Louis Cardinals slugger Mark McGwire had to answer in 1999.

And answer it, he did.

McGwire's 1999 campaign was a banner follow-up to his 1998 explosion, a season that cemented his legacy as a generational superstar.

The 35-year-old first baseman posted a beefy .278/.424/.697 slash line with an MLB-best 65 home runs and an NL-best 147 RBIs.

McGwire's NL-leading RBI total was daffy, considering he only had 145 hits, adding up to the highest RBI-per-hit ratio in Major League Baseball history.

It was another record-shattering year for the mountainous masher.

McGwire extended his MLB record of consecutive 50-home run seasons to four and joined Sosa as the only players to string together back-to-back seasons of 60 homers or more.

The Cards meandered to a mediocre 75-86 record, but McGwire remained a sideshow attraction bigger than wins and losses.

To commemorate each of McGwire's 70 home runs from the previous season, they released seventy variations of card #220, with this one being the most desirable.

1999 Topps #220 Mark McGwire Baseball Card

1999 Topps #75 Tony Gwynn

Estimated PSA 10 Gem Mint Value: $45

In October 1998, Gwynn had his October farewell during a magical Padres run to a National League pennant.

While San Diego crashed and burned in a four-game World Series sweep at the hands of the New York Yankees, Gwynn's mere presence in the Fall Classic felt like a fitting tribute.

However, the heart and soul of San Diego sports would never again play an entire season.

Gwynn was limited to just 111 games in 1999, slashing .338/.381/.477 with 27 doubles, 59 runs scored, seven stolen bases, ten home runs, and 62 RBIs in 446 plate appearances (411 at-bats).

And as he struggled through injury, the Padres ran face-first into a wall.

After winning 98 games and an NL West title in 1998, the Friars slipped to 74-88 in 1999, well out of the playoff mix.

It wasn't all bad news in San Diego, though.

Gwynn was named to his 15th-and-final All-Star Game and notched his 3,000th hit with a first-inning single on August 6th off of Expos starter Dan Smith in Montreal.

In doing so, Gwynn reached the 3,000 Hit Club in fewer games than all but one player (Roberto Clemente) and fewer at-bats than all but one (Wade Boggs).

1999 Topps #75 Tony Gwynn Baseball Card

1999 Topps #270 Cal Ripken Jr.

Estimated PSA 10 Gem Mint Value: $45

After ending his record consecutive games streak at 2,632 games late in the 1998 MLB season, the final stage of Cal Ripken Jr.'s unparalleled Hall of Fame career officially kicked into gear.

Sadly, Ripken's 1999 season began with a heavy heart when his father died of lung cancer just days before Opening Day.

Processing through grief and dealing with a laundry list of nagging injuries, the Baltimore Orioles legend could be forgiven for having an off year.

What's wild about Ripken's 1999 season was that he was perhaps one of the best versions of himself ever seen at the plate (when he could stay on the field.)

Limited to 86 games and 354 plate appearances (332 at-bats), Ripken posted career highs in batting average (.340), slugging percentage (.584), OPS (.952), and OPS+ (144).

If he had been able to keep up that clip at his previous workload of 162 games, his 18 home runs and 57 RBIs would have also projected out to career bests.

Now a 17-time All-Star, it was clear that the punishment Ripken's body took during his 17-year streak was taking its toll.

However, he somehow defied Father Time in 1999 with an impressive part-time performance that buoyed an otherwise ho-hum 78-84 campaign in Maryland.

1999 Topps #270 Cal Ripken Jr. Baseball Card

1999 Topps #277 Rickey Henderson

Estimated PSA 10 Gem Mint Value: $45

After leading the Majors in steals and the American League in walks in 1998 during a one-year return to Oakland, the 39-year-old future Hall-of-Famer signed a two-year deal with the New York Mets.

Under the bright lights of America’s most scrutinizing media market, Henderson set out to back up his bluster with a throwback campaign.

Bolstering one of the Majors’ most talented teams, Henderson posted his best OPS (.889) since 1993.

He slashed a healthy .315/.423/.466 with 30 doubles, 37 stolen bases, 89 runs scored, 82 walks, 12 home runs, and 42 RBIs in 526 plate appearances (438 at-bats).

The Sporting News Comeback Player of the Year, Henderson did it all in the leadoff spot for the 97-win Mets.

That carried over into the first round of the playoffs, too.

Baseball’s all-time steals king was the king of New York against the Arizona Diamondbacks, going 6-for-15 with five runs scored, three walks, an RBI, and six stolen bases in a four-game NLDS triumph.

Yet, as the MLB gods giveth, they taketh away.

Henderson was a virtual no-show in the NLCS against the division-rival Atlanta Braves, hitting just .174 in a stressful six-game defeat.

And ill feelings were further compounded by an alleged incident during the Game 6 clincher in which Henderson was caught playing cards with Bobby Bonilla in the clubhouse.

1999 Topps #277 Rickey Henderson Baseball Card

1999 Topps #291 David Ortiz

Estimated PSA 10 Gem Mint Value: $45

In one of many mind-boggling moves by Minnesota Twins management in David Ortiz's six years with the organization, Ortiz was sent down to Triple-A Salt Lake City before Opening Day in 1999.

It remains baffling.

Despite injury issues, Ortiz was Minnesota's best hitter for large chunks of the 1998 season.

And even though he tore up the Minors to the tune of a.315 average, 30 home runs, and 110 RBIs in 1999, he was called up in mid-September.

By then, Ortiz was fighting through a torn ACL and couldn't meaningfully contribute.

He went 0-for-20 in limited action with 12 strikeouts, looking nothing like the game-breaking Big Papi he'd become.

Without Ortiz, the Twins were an absolute wreck.

They finished with baseball's worst record at 63-97-1 -- a percentage point worse than the bottom-feeding Florida Marlins in the NL East.

There's no reason to believe that a healthy Ortiz, especially at a much more inconsistent point of his career, would have lifted the Twins to anything resembling playoff contention.

However, his impact bat was sorely missed by an offense that finished dead last in the Majors with 4.26 runs scored per game.

1999 Topps #291 David Ortiz Baseball Card

1999 Topps #355 Chipper Jones

Estimated PSA 10 Gem Mint Value: $45

1999 was the year that Chipper Jones put his personal problems aside and delivered an NL MVP season for the ages.

After admitting to infidelity and watching his marriage publicly fall to pieces, Jones became public enemy #1 for rival fans in New York, Philadelphia, and anywhere where the Braves weren't the home team.

Using the derision as fuel, Jones leveled up in 1999.

And he did so with help from new Braves hitting coach Don Baylor.

Seeing that Jones, a natural right-handed swinger, was struggling to connect with power against lefties, he helped Jones morph into a switch-hitting standout able to play the hand advantage when necessary.

It worked amazingly.

Jones hit .352 as a righty with a career-best 15 home runs from that side and ended up setting a National League record for most home runs as a switch hitter with 45.

Jones finished the year slashing .319/.441/.633 with 116 runs scored, 41 doubles, 25 stolen bases, and 110 RBIs.

A near-unanimous selection for NL MVP, Chipper saved his best for the postseason.

And while Jones and the Braves sputtered wildly in a four-game sweep at the hands of the Yankees in the World Series, Chipper's MVP moment was still a positive note in his Hall of Fame career.

1999 Topps #355 Chipper Jones Baseball Card

1999 Topps #34 Nolan Ryan

Estimated PSA 10 Gem Mint Value: $40

Nolan Ryan's playing days were long gone by the time the 1999 Topps baseball set was released, but he still played a significant role in the release.

Collectors could find reprints of all his Topps base cards from 1968 to 1994, easily distinguished by a foil stamp on the front.

In addition, chromium Finest and autograph versions of the cards were inserted randomly to keep the chase even more enjoyable.

Finally, Ryan also appeared on this base card that shows the Hall of Fame hurler winding up and ready to release a blazing fastball.

1999 Topps #34 Nolan Ryan Baseball Card

1999 Topps #95 Pedro Martinez

Estimated PSA 10 Gem Mint Value: $40

Several players can stake claims to the greatest single-season pitching performance of all time.

However, few pitchers (if any) can touch Pedro Martinez's back-to-back Cy Young campaigns of 1999 and 2000.

And the former was a banger for the Boston Red Sox righty as he secured the AL's pitching triple crown, leading the league in strikeouts (313), ERA (2.07), and wins (23), the last two standing as MLB bests.

Martinez was a statistician's dream in 1999.

He also led the American League in hits per nine innings (6.8) and paced the Majors in ERA+ (243), FIP (1.39), WHIP (0.923), strikeouts per nine innings (13.2), strikeout-to-walk ratio (8.46), and home runs per nine innings (0.4).

The 1999 AL MVP runner-up was virtually untouchable, and the Wild Card winners hoped that trend would continue in the playoffs.

Facing Cleveland in a rematch of the previous year's four-game ALDS loss, Pedro fought through back injuries to help lead Boston to a 3-2 series win.

Martinez earned the only Red Sox win of the ALCS against the Yankees, throwing seven scoreless in a much-hyped duel with Roger Clemens that ended up as a 13-1 laugher for the Sox.

The Yankees rolled the Red Sox otherwise, closing the series in five and closing the book on Martinez's second Cy Young season.

1999 Topps #95 Pedro Martinez Baseball Card

1999 Topps #423 Frank Thomas

Estimated PSA 10 Gem Mint Value: $35

After terrorizing American League pitching from 1991-97 and serving as a shortlist candidate for the mantle of "baseball's best hitter," the "Big Hurt" started hurting in 1998 and 1999.

Suffering through several minor injuries, Thomas was relegated to a designated hitter role most of the time.

As someone who loved playing first base, this wore on Thomas and ended up eating into his production at the plate.

Missing just under a month due to rest and injury in '99, Thomas hit .305 in 590 plate appearances (486 at-bats), his ninth .300 season in ten years.

That was the good news.

The bad news was that Thomas' power dipped dramatically.

A regular 30-to-40 home run hitter, Thomas hit just 15 in 1999 and posted a good but not great .885 OPS.

His OPS+ of 125 marked nearly a 50% drop-off from his last All-Star season just two years prior.

It was an underwhelming year for an underperforming 75-win Chicago squad.

After a third straight losing season, things looked bleak for Thomas and the Southsiders heading into the new millennium.

1999 Topps #423 Frank Thomas Baseball Card

1999 Topps #62 Vladimir Guerrero

Estimated PSA 10 Gem Mint Value: $30

When the Montreal Expos traded away Pedro Martinez before the 1998 season, an already beleaguered fan base took another one on their collective chin.

So, it was a great consolation when the Expos paid up to extend Vladimir Guerrero during the 1998 campaign.

Guerrero emerged as the face of the franchise during an otherwise dismal year.

For his efforts, he earned a $28 million contract extension through 2003.

After being rewarded with a new deal, Guerrero rewarded Montreal's fans in 1999.

He put together the longest hitting streak in the Majors in twelve years (31 games) and posted top-ten MLB finishes in home runs (42), RBIs (131), and slugging percentage (.600).

He also finished second in the Majors in total bases (366) for a 68-win Expos team with little else going for it.

Guerrero was the whole show in Montreal in 1999, earning his first All-Star nod, his first Silver Slugger award, and an 11th-place finish in the NL MVP race.

In the waning days of Expos baseball, he was one of the few things that made them worth watching.

1999 Topps #62 Vladimir Guerrero Baseball Card

1999 Topps #172 Mariano Rivera

Estimated PSA 10 Gem Mint Value: $30

One of the greatest closers of any generation, Rivera pitched to a sterling 1.85 ERA in 66 regular-season appearances in 1999 for the back-to-back World Series champs.

When you look deeper at the numbers, Rivera's filthy 1999 campaign gets downright nasty.

Rivera made 28 appearances after July 21st and did not surrender an earned run in any of them.

During that iconic stretch, he held opposing hitters to a minuscule .136 batting average while logging 20 saves.

Now a two-time All-Star, Rivera finished 14th in the AL MVP race and third in the league's Cy Young voting, tops in both categories for relievers.

It was in the World Series, however, where Rivera shined brightest.

The 29-year-old righty pitched all four games of the Yankees' sweep of the Braves, notching a win and two saves across 4.2 scoreless innings.

Named World Series MVP, Rivera became the third pitcher in MLB history to record the last out in back-to-back World Series.

And across 18 combined playoff appearances in 1998 and 1999, he boasted a 0.00 ERA.

Flawless, efficient, and often unhittable, Rivera was something else entirely.

1999 Topps #172 Mariano Rivera Baseball Card

1999 Topps #331 Roy Halladay

Estimated PSA 10 Gem Mint Value: $30

Roy Halladay was an easy choice for a roster spot in 1999.

The question for Blue Jays manager Jim Fregosi was where to put him from day to day.

Halladay's first appearance in 1999 showed his value as a reliever.

On April 7th, the 22-year-old righty dazzled in a three-inning save to finish off the Minnesota Twins, the only save of his Hall-of-Fame career.

But he also pitched great in the starting rotation, notched his first career shutout on May 20th against Detroit, and had a few dominant moments in long form for 84-win Toronto in 1999.

All in all, Halladay split his time equally between the starting rotation and the bullpen, making 18 relief appearances and 18 starts, ending the year with an 8-7 record and a solid 3.92 ERA.

His 1.574 WHIP and 156 hits allowed in 149.1 innings pitched were marks of a young pitcher finding his way.

Without high velocity or a go-to strikeout finisher, Halladay had to learn how to pitch to contact effectively against Big-League talent.

He wouldn't get there for a couple of years, but when he did, Halladay bloomed from a promising prospect to one of the greatest hurlers of the 2000s and early 2010s.

1999 Topps #331 Roy Halladay Baseball Card

1999 Topps #395 Barry Bonds

Estimated PSA 10 Gem Mint Value: $30

The 1999 season was one of the most controversial years of Barry Bonds' career.

And that's saying something.

After working during the offseason with trainer Greg Anderson, later outed as a steroids dealer, Bonds put on a jaw-dropping amount of muscle.

Gone was the slim all-around player of his Pittsburgh days.

In his place was a gargantuan cartoonish slugger with muscles in places that other players didn't have places.

The quick muscle gain came with a price, and Bonds tore his triceps early in 1999 and went under the knife, losing nearly sixty games.

When Bonds was able to play, he was an MVP-caliber slugger like he always was.

In just 434 plate appearances (355 at-bats), Bonds hit .262 with a 1.006 OPS, 34 home runs, and 83 RBIs.

Without Bonds for over a third of the year, the Giants were no match for the Diamondbacks and ended the year as the NL West runner-up with a respectable 86-76 record.

However, that left them 11 games short of a Wild Card spot and 14 games behind the D-Backs in the division.

1999 Topps #395 Barry Bonds Baseball Card

1999 Topps Baseball Cards In Review

With a checklist that included just 462 cards, the 1999 Topps baseball set isn't nearly as large as some of the others of the 1990s.

And, other than Matt Holiday, A.J. Burnett, and Pat Burrell, there really aren't any notable rookie cards to be found inside.

Still, there are plenty of stars and Hall of Famers to keep things interesting.

The 70 variations of Mark McGwire's card #220 and 66 variations of Sammy Sosa's card #461 that commemorated McGwire's 70 home runs and Sosa's 66 from the 1998 season was a nice touch, too.

Unopened Box of 1999 Topps Baseball Cards

There are several subsets within the checklist, including:

  • Season Highlights (#200 - 204)
  • Prospects (#205 - 212; #425 - 437)
  • Draft Picks (#213 - 219; #438 - 444)
  • McGwire's 70 Home Runs (#220)
  • League Leaders (#221 - 232)
  • World Series (#230 - 240)
  • Checklists (#241 and #242; #462 - 463)
  • Strikeout Kings (#445 - 449)
  • All-Topps (#450 - 460)
  • Sammy Sosa's 66 Home Runs (#461)

Some may think the design is too simple, but I've always liked this set's overall look and feel as the gold borders are a nice change.

I think if the set had one or more Hall of Fame rookies inside its checklist, it would get a lot more attention than it does these days.

Still, it's a decent set overall for the die-hard collector.

Ross Uitts

Ross is the founder of Old Sports Cards and has been collecting sports cards for over 30 years. He also loves to write about the hobby and has written for Beckett, Topps, SABR and of course, this website. Need help buying or selling cards or have a general question about the hobby? Contact him at [email protected]

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