If you’re a fan of change, then 1999 Topps baseball cards may not have seemed all that exciting when they were first issued.

After all, the new Topps cards had a lot in common with their direct predecessors — 1998 Topps baseball cards.

In particular, Topps carried over the gold-brown borders, set-long single-player tribute, modest design elements, and two-series format from 1998 to 1999.

But, hey, at least they varied the checklist a bit, paring it down from 503 cards in ’98 to a tidy 462 in 1999.

And there were a few goodies in the 1999 set that were missing from the 1998 version (and vice versa), some of which we’ll talk about here in a few minutes.

So, for all of the repeats, and all of the sameness and overproduction that seem to permeate card issues from the 1990s, there are still plenty of reasons to collect 1999 Topps baseball cards … and plenty of collectors who still seek them out … and even plenty of dollars still flowing their direction.

What follows, then, is a list of the most valuable 1999 Topps baseball cards by measure of recent sales for PSA 10 copies. We’ll start at the bottom of the pile and work our way up to the most expensive of them all, while keeping our focus on base cards (as opposed to the many parallels, inserts, and other “specials” the set has to offer).

(Note: The following sections contain affiliate links to eBay and Amazon listings for the cards being discussed.)

1999 Topps Nolan Ryan (#34)

1999 Topps Nolan Ryan

Five years after his last appearance in a base Topps set, Nolan Ryan was back to greet his adoring hobby public here in the 1999 issue.

Picking up on the theme they had established with Roberto Clemente the year before, Topps carted out a full Ryan tribute as The Express rolled toward Hall of Fame induction that summer.

Among the pieces in said tribute were reprints of Ryan’s base Topps cards from his playing career, Finest versions of those reprints, Refractor versions of those Finest cards, and a run of Ryan autographs, all spread between Series One and Series Two.

And then there was this actual base card, which Topps slid right into their regular lineup at #34 – yeah, that had been Ryan’s uniform number with the Houston Astros and Texas Rangers.

Naturally, collectors ate up all the new Ryan material, and we still love it all today.

Value: $30-35

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1999 Topps Mike Mussina (#180)

1999 Topps Mike Mussina

By 1999, Mussina had established himself as one of the most consistently excellent pitchers in the game, having paced the Orioles rotation for most of a decade.

In 1998, he had put up a modest season by his standards – 13-10, 3.49 ERA – but at least he still managed to snag his third consecutive Gold Glove award.

Mussina’s 1999 returns were a bit better, as his 18-7, 3.50 ERA showing was good enough for a second-place finish in American League Cy Young voting that fall.

A couple years later, of course, Moose signed as a free agent with the Yankees and went on to be a key contributor for several playoff teams (though no World Series winners).

That Bronx run provided enough of a profile boost to get Mussina’s cards perking with collectors and certainly didn’t hurt his chances at a Cooperstown plaque, which he snagged in 2019.

Value: $35-40

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1999 Topps Jim Thome (#380)

1999 Topps Jim Thome

Thome entered the 1999 season as a beloved figure in Cleveland, one of the key contributors in the Tribe’s return to contention during the 1990s.

But, for as good as Thome had been, regularly blasting 30-40 home runs while driving in and scoring around 100 runs each season, his really BIG numbers lay just ahead.

To wit …

After smacking 33 long balls in 1999 and 37 in 2000, Thome would ramp up the power in the new decade with homer totals of 49, 52, 47, and 42 before injury curtailed his playing time in 2005.

The latter two of those totals came for the Phillies after the big first baseman signed a free agent deal with Philly ahead of the 2003 season. That move not only gave Thome a new challenge, it also gave him a chance to endear himself to a whole new fanbase.

Mission accomplished.

The added exposure also helped elevate Thome’s hobby profile and, today, as a Hall of Famer, he is as popular with collectors as ever.

Value: $35-40

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1999 Topps Tony Gwynn (#75)

1999 Topps Tony Gwynn

Gwynn saw his streak of four straight National League batting titles snapped in 1998, when he could muster *only* a .321 average in 127 games for the Padres.

That was a steep dropoff from the gaudy .372 mark he put up in 1997, but it was still miles ahead of what mere mortals could ever hope to accomplish even in their best seasons.

Still, Gwynn’s 148 hits left him within hailing distance of 3000 hits, and he’d continue his quest in 1999 while collectors were pulling this sunny card of Mr. Padre.

By then, of course, his hobby legacy and Hall of Fame track were well established, and collectors still love Gwynn and his pasteboards today.

Value: $35-50

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1999 Topps Derek Jeter (#85)

1999 Topps Derek Jeter

In 1998, Jeter hit .324, smacked 19 home runs, drove in 84 runs, scored 127 times, and stole 30 bases to help the Yankees put up an incredible 114-48 record and win their second World Series title in three years.

That was all good enough to leave Captain Clutch third in American League Most Valuable Player voting and to ratchet up his standing with collectors even higher than his 1996 Rookie of the Year Award and solid 1997 follow-up had already done.

Here we see Jeter running toward second during what would be his first (of 14) All-Star seasons, a classic shot that strums hobby memories all these years later.

Value: $35-50

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1999 Topps Mariano Rivera (#172)

1999 Topps Mariano Rivera

This is a pretty frightening baseball card.

I mean, by 1999, we all knew that Rivera was probably the best reliever in the game, and he had certainly been a key contributor to the Yankees’ World Series championships in 1996 and 1998.

If you were a batter, you could look at his sub-2.00 ERA and batting-average-against right around .200 and just weep, or at least wring your hands in the darkness where Mo couldn’t see you fret.

But here, Rivera gives us a glimpse of what might happen to you if you DID manage to get out of the batter’s box against him. He’s in full-on linebacker mode, and his eyes are on the prize – an open-field tackle between home plate and first base is in your future.

In this card’s future?

A gradual increase in collector appreciation for the man and his pasteboards across the board, to the point that Hall of Famer Mo now has plenty of dedicated fans in the hobby ranks.

Even if this is the scariest among all 1999 Topps baseball cards.

Value: $40-50

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1999 Topps David Ortiz (#291)

1999 Topps David Ortiz

Ortiz spent three years in the Seattle Mariners’ minor league system, where he was known as “David Arias.”

Upon being traded to the Minnesota Twins in 1997, though, the young slugger made it be known that he preferred to use his father’s last name, Ortiz, rather than his mother’s (Arias).

That summer, his power ballooned, and he smacked 31 home runs in three minor league stops, earning him a September call-up to the Twinkies. He hit .327 in 15 games, then managed .277 in 86 games with Minnesota the following season, his official rookie campaign.

That’s where we find the still-fairly-slender first baseman on this card, which fittingly shows him at the end of a mighty swing rather than in the field.

Ortiz, of course, would go on to become one of the game’s most celebrated designated hitters after signing a free agent deal with the Boston Red Sox in January of 2003 following an outright release by the Twins in December of 2002.

When he helped the Sox end their “Curse of the Bambino” by winning the 2004 World Series, Big Papi sent collectors scurrying to find his early career issues, including his 1997 rookie cards and his other Twins entries, like this one.

Today, with a Cooperstown plaque under his prodigious belt, Ortiz is a collector favorite, and his cards never linger unsold for long.

Value: $40-50

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1999 Topps Cal Ripken Jr (#270)

1999 Topps Cal Ripken Jr

This was the first base Topps card picturing Ripken after his consecutive-games streak ended in September of 1998, and it was sort of a bittersweet sight for collectors.

On the one hand, seeing an aged and gray Cal standing flat-footed in the infield reminded us just how much time had passed since he helped redefine what a major league shortstop could be. And just how close the end of his career might be.

But on the other hand, it was a Cal Ripken, Jr., baseball card. And it was always a good day when you could pull one of those from a pack, or hold one in your hands, or even just see a picture of one.

Still is.

Value: $40-55

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1999 Topps Rickey Henderson (#277)

1999 Topps Rickey Henderson

After an extended (for him) stay in San Diego in 1996 and 1997, and following a cameo with the Angels to wrap up that latter season, Rickey spent 1998 back in Oakland.

Like always.

But, by the time Topps cranked up their 1999 printing presses, Rickey was an employee of the New York Mets, having signed as a free agent in December of 1998. This card managed to capture that new affiliation, though to be fair, you can’t really see the logo on Rickey’s cap here.

Regardless of whether there’s some creative angling at play on this card or not, there’s no denying that Henderson remained a top hobby draw in 1999 even as the sport and fandom and collectors rattled on about all the home runs rattling rafters in stadiums across the land.

Today, cards like this from Henderson’s late-career tour of the majors remind us how we thought he might play forever … and how you can never *really* be sure a comeback isn’t just around the corner.

Value: $50-60

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1999 Topps Ken Griffey Jr (#100)

1999 Topps Ken Griffey Jr

While Mark McGwire and Sammy Sosa were chasing Roger Maris over in the National League during the summer of 1998, Junior mounted a sort of quiet assault on the American League home run record.

In the end, he’d match his 1997 total of 56 dingers, chipping in 146 RBI and scoring 120 times himself. Griffey also stole 20 bases, amazingly reaching the 20-20 club for the first time in his storied career.

Of course, even at the young age of 28, Griffey had pretty much already cemented his legacy, and his 1989 Upper Deck rookie card was a hobby legend.

That all made every other Junior card a must-have, and this dramatic 1998 Topps base card carries that classic air today.

Value: $60-70

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So, does your favorite appear on this list of the most valuable 1999 Topps baseball cards? If not, I’d love to hear your picks!

1999 Topps Baseball Card Pick (Base) 1-254

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Derek Jeter 1999 Topps Baseball New York Yankees #85

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