Revved Up (2005)

Though not a Challenges release as such, can be considered to be its predecessor as it follows much of the same format. It contains challenges from Series 3 through to Series 5 of Top Gear.

Chapter 2 - Mitsubishi Evo vs. Bobsleigh (S05E08)
Chapter 3 - Race to Monte Carlo (S04E01)
Chapter 4 - Lotus Exige vs. Apache (S04E01)
Chapter 5 - People Carrier Racing (S05E05)
Chapter 6 - Cheap Porsche Challenge (S05E06)
Chapter 7 - VW Golf vs. Lightning (S04E05)
Chapter 8 - Jet vs. Mondeo & 2CV (S04E08)
Chapter 9 - Destroying a Toyota Hilux (S03E05 - S03E06)

Volume 1 (2007)

The first Challenges DVD contained challenges from Series 7 through to Series 9, picking up where the Revved Up compilation from 2005 left off.

Chapters 2, 3, 4 - Race to London (S07E05)
Chapters 5, 6, 7, 8, 9, 10, 11 - Italian Supercar Challenge (S07E04)
Chapter 12 - Peugeot vs. Parkour (S08E07)
Chapters 13, 14, 15, 16 - Limousine Challenge (S09E06)
Chapters 17, 18, 19 - Reliant Robin Rocket (S09E04)
Chapter 20 - Porsche Cayenne vs. Parachutists (S08E04)
Chapters 21, 22, 23 - Convertible People Carrier (S08E01)
Chapters 24, 25, 26 - Amphibious Car Challenge (S08E03)

Volume 2 (2008)

Volume 2 contains challenges exclusively from Series 10. It is the only such release to contain challenges specifically from one series of the show.

Chapters 2, 3, 4, 5 - Amphibious Car Challenge II (S10E02)
Chapters 6, 7, 8 - Bugatti Veyron vs. Jet Race (S10E03)
Chapters 9, 10 - Race Across London (S10E05)
Chapters 11, 12, 13 - Motorhome Racing (S10E06)
Chapters 14, 15, 16, 17, 18, 19 - Greatest Driving Road Search (S10E01)
Chapters 20, 21, 22 - Fiat 500 vs. BMX Bandits (S10E09)
Chapters 23, 24, 25, 26, 27, 28 - Britcar 24 Hour Race (S10E09)

Volume 3 (2008)

Volume 3 contained challenges from Series 10 through to Series 12, which had only recently finished airing at the time of release. Each chapter begins with an odd-sounding Jessica sting, which is almost techno-like, and is actually the remnants of Ian Morris' vetoed Top Gear theme which Jeremy Clarkson hated.

Chapter 2 - Cheap Alfa Romeos (S11E03)
Chapters 3, 4 - British Leyland Challenge (S10E07)
Chapter 5 - GT-R vs. Bullet Train (S11E04)
Chapter 6 - Top Gear vs. D-Motor (S11E06)
Chapter 7 - Lorry Challenge (S12E01)
Chapter 8 - Richard Drives an F1 Car (S10E08)
Chapter 9 - Terios Fox Hunting (S11E05)
Chapter 10 - Best Bus Race (S12E05)

Volume 4 (2010)

Volume 4 was almost entirely Series 13, with one challenge from Series 14, and a "stray" challenge from Series 11.

Chapter 1 - Race to the North (S13E01)
Chapters 2, 3 - Homemade Electric Car (S14E02)
Chapters 4, 5 - Cheap RWD Cars (S13E05)
Chapter 6 - Police Car Challenge (S11E01)
Chapters 7, 8 - Classic Rally Cars in Mallorca (S13E06)

Its bonus disc contained a few other key challenges from Series 11 through 13.

Chapter 1 - Ford Fiesta Review (S12E06)
Chapter 2 - Communist Cars (S12E06)
Chapter 3 - James Meets Ken Block (S13E03)
Chapter 4 - Audi RS6 vs. Skiers (S11E02)
Chapter 5 - Ferrari Daytona vs. Powerboat (S12E05)
Chapter 6 - Ultimate Drag Race: Veyron vs. F1 (S13E02)

Volume 5 (2011)

Volume 5 contains challenges which straddle the gap between SD and HD, ranging from Series 13 through to Series 15, with one Series 16 challenge right at the end.

Chapters 1, 2 - Motorhome Challenge (S15E04)
Chapter 2 - VW Scirocco Advert (S13E07)
Chapters 3, 4 - British Sports Cars (S15E06)
Chapters 5, 6 - Sports Saloon Challenge (S15E02)
Chapter 7 - Touareg vs. Swedish Youths (S15E05)
Chapter 8 - Bugatti Veyron Super Sport Test (S15E05)
Chapter 9 - Caravan Airship (S14E03)
Chapter 10 - Airport Race (S14E04)
Chapter 11 - Renault Twingo Test (S14E04)
Chapter 12 - Toyota Hilux on Icelandic Volcano (S15E01)
Chapter 13 - Reliant Robin Drive (S15E01)
Chapter 14 - VW Beetle Drop Test (S16E01)

The bonus disc contained a few other memorable moments from Series 15.

Chapter 1 - Tom Cruise and Cameron Diaz SIARPC segment (S15E05)
Chapter 2 - Lewis Hamilton drives the MP4/4 (S15E05)
Chapter 3 - Rubens Barrichello's uncut SIARPC lap (S15E03)
Chapter 4 - Bugatti Veyron Super Sport speed record (S15E05)
Chapter 5 - Germany to Poland Economy Test (S15E02)
Chapter 6 - Reliant Robin Flip (S15E01)
Chapter 7 - Jeremy Clarkson avoids a crash (S15E01)
Chapter 8 - James May deflates the Hilux's tyres (S15E01)
Chapter 9 - James shovels a lava flow (S15E01)
Chapter 10 - British Sports Car "Crash Test" (S15E06)

Volume 6 (2012)

Volume 6 contains challenges almost exclusively from Series 16 and 17, with one stray challenge from Series 13 seemingly omitted from previous installments. Series 18 had already aired by this point, but none of its challenges were included on the main disc.

Chapter 1 - Top Gear Ashes (S16E02)
Chapter 2 - Car Trains (S17E04)
Chapter 3 - Teenage Car Challenge (S13E02)
Chapter 4 - Snowbine Harvester (S16E05)
Chapter 5 - Four-seater Convertibles (S16E04)
Chapter 6 - Demolition Challenge (S17E05)
Chapter 7 - Skoda Yeti Test (S16E01)
Chapter 8 - Mini vs. Skeleton Bob Racer (S17E01)
Chapter 9 - Marauder Test (S17E01)
Chapter 10 - Jaguar vs. God Race (S16E06)
Chapter 11 - Range Rover Evoque Test (S17E03)
Chapter 12 - Race2Recovery Rally Team (S17E06)
Chapter 13 - Jaguar E-Type Tribute (S17E01)

Its bonus disc however contained segments as early as Series 3 and as late as Series 18.

Chapter 1 - Black Stig's Death (S03E01)
Chapter 2 - Rig Stig (S12E01)
Chapter 3 - Janet Stig-Porter (S14E02)
Chapter 4 - Eurospeedway Lausitz Track Day (S15E02)
Chapter 5 - Chinese Stig (S18E02)
Chapter 6 - The Stig's American Cousin (S09E03)
Chapter 7 - The Stig's African Cousin (S10E04)
Chapter 8 - The Stig's Italian Cousin (S18E01)
Chapter 9 - Communist Stig (S12E08)
Chapters 10, 14 - Ryan Reynolds' cut SIARPC footage (S18E03)
Chapter 11, 15 - Sebastian Vettel's cut SIARPC footage (S17E03)
Chapter 12 - Jonathan Ross' cut SIARPC footage (S16E03)
Chapter 13 - Alice Cooper's cut SIARPC footage (S17E01)
Chapter 16 - Ross Noble's cut SIARPC footage (S17E02)
Chapter 17 - The Interceptors (S17E05)
Chapter 18 - Amy Williams' Uncut Run (S17E01)
Chapter 19 - Slow-mo Ice and Sand Compilation (Various)
Chapter 20 - SAAB vs. Jet II (S18E05)
Chapter 21 - Shooting a Marauder (S17E01)
Chapter 22 - Intercourse (East Coast Road Trip)