MINT 2023
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Top 1999 Baseball Cards to Collect

Top 1999 Baseball Cards to Collect

The year 1999 gave us The Matrix, Britney Spears and Eminem, the Y2K scare, and the Yankees repeating as World Series champions. On the hobby front, the 1999 baseball card scene continued to evolve and modernize with multiple licensed manufacturers hoping to reach the hearts and wallets of collectors. There were three major trends appearing across the daunting number of new products. While there were a few popular rookie cards in 1999, the real story was the push to make more exclusive, high-end cards of superstar players, more certified autographs, and a growing nostalgia for cards of Hall of Famers. This shift is made clear in the Top 1999 Baseball Cards list below.

Collectors had a wide array of products available to them through four major licensed companies: Fleer, Pacific, Topps, and Upper Deck. Each of the manufacturers had numerous brands that were aimed at a variety of different collectors. There were more than 50 major product releases in 1999, with several having a large influence on the hobby that is still visible today.

The majority of baseball card sets in 1999 offered a base parallel and hard-to-find insert cards. Many manufacturers started using tiered parallels that ranged from having serial-numbered quantities in the hundreds all the way down to printing plates, which were one-of-one editions. Insert cards had a similar distribution as parallels, with some having a high quantity while others were very rare with long packs odds. Although current collectors are very familiar with these types of cards, the concept was in its infancy in 1999. Many of these cards from the late 1990s are still very popular, especially those looking for high-end cards from Hall of Famers.

View 1999 baseball card auctions with the most bids on eBay.

The baseball card hobby had plenty of exposure to certified autographs before 1999, but in keeping up with the competition, card manufacturers made player signatures more available with a focus on former Hall of Fame players. Fleer's Greats of the Game led the way with a great checklist and Cooperstown stars from the 1950s through the 1980s. Upper Deck Century Legends was another autograph-centric product with a deep checklist focused on all-time greats from yesteryear.

Perhaps the most important influence seen with 1999 baseball cards is the popularity of cards showcasing older players on retro designs. Fleer produced a line of Stan Musial insert cards with a parallel set of autographs to go along with the aforementioned Greats of the Game. Beyond Century Legends, Upper Deck also created a set of relic cards featuring the members of the 500 Home Run Club that are still in demand. Topps generated insert sets across several brands combining old card designs with art, along with a few inserts that were reprinted Topps cards of Hall of Fame players. The popularity of these cards in 1999 has resulted in exponential growth for these types of products.

This top cards list from 1999 looks at some of the very best the hobby had to offer from numerous products that are still treasured by collectors and have influenced the current designs and checklists of modern manufacturers.

Top 1999 Baseball Cards to Collect

Bolded links go directly to detailed product profiles or player guides when available. Shop for singles or check completed sales prices using the specific card links.

10. 1999 Bowman Chrome Refractor Josh Hamilton RC #431

The Devil Rays selected Josh Hamilton out of high school with the first pick in the 1999 MLB Draft. He was immediately labeled as a "can't miss prospect." Collectors flocked to Hamilton's cards and he became one of the most popular figures in the hobby. His Bowman Chrome rookie card was one of the first to elevate the popularity of the brand. Bowman Chrome looked different in 1999 with the absence of autographs, but there were still Refractors and other parallels for collectors to chase, including the International (#/100) and Gold (#/25) Refractors.

Hamilton's Bowman Chrome Refractor rookie reached its peak in the hobby world during his MVP season and the Rangers' back-to-back run to the World Series in 2010 and 2011. Of course, the end of Hamilton's career had a sharp decline which lowered his profile within the hobby. There were also multiple off-the-field issues for the controversial player.

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9T. 1999 Topps Mark McGwire Home Run Variation #220

9T. 1999 Topps Sammy Sosa Home Run Variation #461

Variations have become commonplace in the modern Topps flagship sets, but that was not always the case. Many of the variations that appeared before 2000 were unintentionally created through production errors. In 1999, Topps released a well-received pair of cards to celebrate the 1998 home run chase between Mark McGwire and Sammy Sosa. Topps issued 70 different variations for the McGwire HR Record card, one for each of the home runs he hit in 1998, along with 66 variations for Sosa's HR Parade series. While set collectors just need to find a single copy of the McGwire and Sosa cards to achieve their goal, many in the hobby world tried to assemble a complete run of all the home run cards.

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The more significant home run milestone cards carry a premium with collectors, especially the 60th, 61st, and 62nd home run cards of both Sosa and McGwire, along with the 66th for Sammy and 70th for Big Mac. The full run of McGwire and Sosa home run variation cards are also available in the 1999 Topps Chrome set. In addition, collectors can find the 66th and 70th home run cards for McGwire and Sosa, without variations, in both Topps Super Chrome and Topps Opening Day.

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8. 1999 UD Black Diamond Mark McGwire A Piece of History Bat #MM

The Black Diamond Baseball brand only ran for two years, but its 1999 debut release was memorable. Mark McGwire was one of the most popular figures in the hobby at this time, but he had not appeared in a product as a certified autograph signer, nor was there a memorabilia card produced. Upper Deck decided to step up and purchased a Mark McGwire bat for use in a relic card for 1999 Black Diamond.

The Cardinals' slugger was apparently not happy with Upper Deck's decision to create the card using his bat. The back even specifies that "this bat was not obtained directly from Mark McGwire, but was obtained from a third-party source." The card is not only tough to find, but the controversy surrounding the card has added to its popularity.

Upper Deck would eventually sign Mark McGwire to an autograph and memorabilia deal in 2002 after he had retired from the game. Game-used relic cards from the late 1990s and early 2000s are generally inexpensive and easy to find, but this card breaks that norm with a high price tag and limited supply on the secondary market.

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7. 1999 SP Signature Edition Mariano Rivera Autograph #MRI

Following his retirement from the Yankees in 2013, Mariano Rivera has appeared in various baseball card products on the autograph checklist. For many collectors, it was a welcome sight as the Hall of Famer's signature was rare throughout the majority of his playing career. However, the more recent Rivera autographs are often tough pulls with low print runs. Earlier in his career, "The Sandman" appeared in several autograph-based sets, most notably 1996 Leaf Signature Series. Rivera's final appearance in a per-pack autograph product was 1999 SP Signature Edition. Released at a time where Rivera's profile as a player was on the rise with the dominance of the late-1990s Yankees, this certified autograph remains one of the Hall of Fame closer's most popular cards on the secondary market. The card is plentiful and raw copies are amongst his least expensive certified autographs.

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6. 1999 Topps Gallery Heritage Hank Aaron #TH1

The original Topps Gallery brand ran from the mid-1990s through the early 2000s. The product's art theme made it popular in some circles of the hobby world. However, 1999 Topps Gallery broke free from being a niche product, gaining wider popularity in large part due to the Gallery Heritage insert cards. Combining spectacular artwork and the design from the 1953 Topps set, it's not hard to draw a line between the popularity of these cards the creation of the Topps Heritage brand in 2001. The checklist for the Gallery Heritage is full of Hall of Fame players, such as Greg Maddux, Cal Ripken, Jr. and Ken Griffey Jr. However, Hank Aaron is the lone retired player to appear in the set.

The Gallery Heritage Hank Aaron insert is not only a great-looking card, but the artist did a spectacular job of drawing in the Hall of Famer's history with the Braves, the Braves franchise history, and the Braves cards in 1953 Topps. The artwork on this card shows Aaron in a Boston Braves uniform, which is the team he signed with in June of 1952 as a middle infielder. The 1953 Topps set was also the last to feature the Boston Braves. Aaron's rookie card arrvived in 1954 Topps, making it one of the first Milwaukee Braves cards. Collectors can also track down the Artists Proof version of this card, which has a Chrome finish, or the limited Lithograph (#/600) that was available through a mail-in offer in packs of Gallery Heritage cards.

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5. 1999 Topps Traded C.C. Sabathia Autograph #T33

The 1999 Topps Traded set was the first Traded MLB product since 1995. Collectors could purchase these cards complete with one autograph per box. One of 75 rookies who signed for this product, C.C. Sabathia's autograph has long been popular with collectors but was overshadowed for years by players like Josh Hamilton, Adam Dunn and Carl Crawford. While all of the aforementioned players had long, productive careers, Sabathia stands out as the most likely to receive Hall of Fame consideration. The former Indians and Yankees hurler does have numerous 1999 baseball cards, but Sabathia's Topps Traded autograph is his lone certified Major League signature produced that year. The card is plentiful, and given the fact that he is likely going to be a popular candidate for Cooperstown, this would be a great addition to any collection.

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4. 1999 Topps Stadium Club Co-Signers Autograph Derek Jeter/Chipper Jones #CS4 AU

High-quality photography and high-end touches helped Stadium Club's popularity in the first half of the decade. Topps added the Co-Signers autographs in 1997. The dual autograph insert set raised the status for the long-running product. Throughout the late 1990s and into the early 2000s, the autograph checklist for Co-Signers featured some great pairings for both team and player collectors. The lineup for the 1999 set was deep, but the dual autograph of Derek Jeter and Chipper Jones is one of the must-have autographs from the late 1990s. The Co-Signers Derek Jeter/Chipper Jones autographs were not serial numbered and they still show up frequently on the secondary market. Naturally, this is a high-end card, but well worth the expense for die-hard collectors from this era.

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3. 1999 Fleer Sports Illustrated Greats of the Game Autographs Willie Mays Autograph

Sports Illustrated teamed up with Fleer to enter the baseball card market in 1997. Their run in the hobby was brief, but it made a huge impact with the creation of the Greats of the Game autograph set. There were 80 Greats of the Game autographs in all, ranging from Hall of Famers like Frank Robinson, Reggie Jackson and Nolan Ryan, to star players like Dave Parker and Graig Nettles, who have lacked the votes to get to Cooperstown but are popular with baseball fans and collectors. The crowning gem of this deep checklist was the autograph of Hall of Fame outfielder Willie Mays.

The card follows the standard design from this set with a past Sports Illustrated cover taking up the top of the card and a blank white space for the signature at the bottom. This is one of Mays' most popular autographs on the secondary market, but it can be a tough find with many copies of this card finding a home in baseball card collections long ago.

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2. 1999 Upper Deck Century Legends Autographs Ted Williams Epic Signatures #TW #/100

1999 Upper Deck Century Legends has one of the most important autograph sets ever produced. Century Legends featured the 50 best players from the 20th century and the 50 greatest active players at the time, with a few prospect cards thrown in. These groups were used to produce the autograph checklist, which is a masterful mash-up of all-time great Hall of Famers and the best active players from the late 1990s. The autograph cards display a black-and-white photograph of the player with an on-card signature.

Ted Williams did not make many appearances in certified autograph products, so it was a notable event when he appeared on a checklist as a signer. It is worth mentioning that Williams only autographed cards for the "Century" parallel. These gold-tinted cards were limited to just 100 hand-numbered copies. While this Ted Williams card still appears on the secondary market from time to time, it's naturally one of the Red Sox Hall of Famer's most popular cards and comes with a steep price tag.

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1. 1999 Upper Deck A Piece of History 500 Club Babe Ruth

The talk of the baseball card world in 1999 was Upper Deck's 500 Home Run Club set. The relic cards were scattered across the different Upper Deck brands released during the 1999 and 2000 calendar years. All 500 Home Run Club members as of 1999 were included, from Eddie Murray, who was the most recent member of the club at the time of the set's release, to the first member of the exclusive club, Yankees slugger Babe Ruth.

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This was another controversial relic card at the time because many baseball collectors disagreed with Upper Deck's decision to buy a Babe Ruth bat and use it to produce bat relic cards. Regardless, the Babe Ruth HR Club card was highly sought after, but naturally a tough find and very expensive when it came up for sale. The popularity of relic cards has wavered over time, but the market for the A Piece of History Babe Ruth bat relic card remains strong and this is considered by many to be one of the best game-used cards ever produced.

A second A Piece of History version for Ruth that is not directly tied to the 500 Club is easier to track down but is also still quite rare and valuable.

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Eric Bracke opened his first pack of cards during the summer of 1983 and has not stopped since, dabbling along the way in a few other sports. His writing career started in 2012 when he started The Snorting Bull Baseball Card Blog.

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