| America Takes to the Road | |
| Best in Class | 1907 Packard 30 Runabout, owned by Herbert A. Lederer of Barrington Hills, IL |
| Tall Grass Award of Distinction | 1910 Ford Model T Touring, owned by John & Mary Ellen Barr of Deer Park, IL |
| Between the Wars | |
| Best in Class | 1937 Austin 7 Nippy 2-Seater, owned by Robert & Marianne Anderson of Barrington, IL |
| Tall Grass Award of Distinction | 1932 Ford Model 18 Phaeton, owned by Ron Schneider |
| Prosperity on Wheels | |
| Best in Class | 1933 Packard Model 1005 Coupe Roadster, owned by Terry Love of Ottawa, IL |
| Tall Grass Award of Distinction | 1931 Cadillac Model 12 Roadster, owned by F.A. “Woody” Rohrbach of Emmaus, PA |
| Tall Grass Award of Distinction | 1930 Packard 7-45 Roadster, owned by Kent Marburger of Palatine, IL |
| Tall Grass Award of Distinction | 1932 Packard 900 Coupe Roadster, owned by Frank & Ann Huntington of Hoffman Estates, IL |
| The Classic Grows Up | |
| Best in Class | 1939 Lincoln Zephyr Coupe, owned by James & Gail Manz of Mundelein, IL |
| Tall Grass Award of Distinction | 1940 Buick 81C Limited 4-Door Phaeton, owned by George F. Voris of Elgin, IL |
| Tall Grass Award of Distinction | 1935 Auburn 851 Cabriolet, owned by Paul & Jean TerHorst of Mundelein, IL |
| The Elemental Sports Car | |
| Best in Class | 1953 Chevrolet Corvette Convertible, owned by C. Davis & Susan Nelsen II of Barrington, IL |
| Tall Grass Award of Distinction | 1957 Porsche Speedster 2-Door, owned by Mike & Kathy Moses of Warrenville, IL |
| Tall Grass Award of Distinction | 1950 Healey Silverstone Roadster, owned by David K. Hans of Barrington, IL |
| Power & Grace: American Horsepower | |
| Best in Class | 1965 Shelby 427 Cobra, owned by Jeff Boston of Wheaton, IL |
| Tall Grass Award of Distinction | 1967 Chevrolet Corvette Coupe, owned by Steve A. Bramati of Deer Park, IL |
| Power & Grace: European Power | |
| Best in Class | 1957 Ferrari 410 Super America Coupe, owned by Chris LaPorte of Beecher, IL |
| Tall Grass Award of Distinction | 1957 Maserati A6G 2000 Grand Sport, owned by John & Lisa Weinberger of Naperville, IL |
| European Style | |
| Best in Class | 1937 Delahaye 135 M Cabrolet, owned by Malcolm Pray of Greenwich, CT |
| Tall Grass Award of Distinction | 1948 Delahaye 135M 3-Position Drophead owned by Kent Shodeen of Geneva, IL |
| Tall Grass Award of Distinction | 1936 Rolls Royce Phantom II 3AX 151, owned by Vincent & Catherine Minogue of Northbrook, IL |
| From Boards to Banking | |
| Best in Class | 1915 Duesenberg Board Track Racer, owned by Joe Freeman of Brookline, MA |
| Tall Grass Award of Distinction | 1932 Miller V-16 Indianapolis Racer, owned by Charles Davis Jr. of Mokena, IL |
| Post-War Dreams | |
| Best in Class | 1954 Kaiser Darrin Roadster, owned by James & Gail Manz of Mundelein, IL |
| Tall Grass Award of Distinction | 1956 Oldsmobile Super 88 Convertible, owned by John Holsteen of Barrington Hills, IL |
| Tall Grass Award of Distinction | 1957 Ford Thunderbird Convertible/Hard Top, owned by Darrel Burnett of Rockford, IL |
| Thinking Outside the Box | |
| Best in Class | 1955 Messerchmitt KR200 Kabinroller, owned by Jim Garbo of Franksville, WI |
| Tall Grass Award of Distinction | 1958 Volkswagen Type 117 Sunroof Sedan, owned by Jonathan Hansen of Madison, WI |
| Tall Grass Award of Distinction | 1958 BMW Isetta Coupe, owned by Joe Rodriguez of Lincolnwood, IL |
| Above the Limit | |
| Best in Class | 1982 Ferrari 512 BBI, owned by Dave Bendl of Harwood Heights, IL |
| Tall Grass Award of Distinction | 1974 Ferrari 365 GT4/BB, owned by Gene Berns of Chicago, IL |
| Tall Grass Award of Distinction | 1969 DeTomaso Mangusta Coupe, owned by Daryl Adams of Barrington Hills, IL |
| Best Long-Distance Touring Car |
| 1932 Buick Model 95 Sports Phaeton, owned by the Tatarowicz Family of Hinsdale, IL |
| Most Elegant Closed Car |
| 1938 Talbot-Lago Tear Drop Coupe, owned by Joe & Angela Cantore of Oak Brook, IL |
| Most Elegant Open Car |
| 1939 Bugatti T57-C 3 Position Drophead Coupe, owned by Dr. James and Martha Foght of Barrington Hills, IL |
| Most Innovative Design |
| 1936 Auburn 852 owned by Dr. James and Martha Foght of Barrington Hills, IL |
| Most Melodious Car |
| 1954 Buick Skylark Sport Convertible, owned by Brad Buell of Libertyville, IL |
| People's Choice Award |
| 1938 Talbot-Lago Tear Drop Coupe, owned by Joe & Angela Cantore of Oak Brook, IL |
| Hagerty's Youth Judges Awards |
| 1965 Shelby GT350, owned by Mike Nowak of Elgin, IL |
| 1959 Porsche 356A Convertible, owned by George and Meg Pierce of Barrington Hills, IL |
| 1957 BMW Isetta 300, owned by Jim & Pat Lichter of Park Ridge, IL |