History Trivia / WinLoseOrDraw

** Several weeks of the Bert Convy version were missing in action on GSN, possibly due to celebrity clearance issues. Clips of them were shown in early GSN promos. They included Sally Struthers & Vicki Lawrence Vs. Ed Marinaro & Charles Nelson Reilly, Loni Anderson & Martha Raye Vs. Burt Reynolds & Charles Nelson Reilly, Edie [=McClurg=] & Donna Pescow Vs. Pat [=McCormick=] & Paul Williams, and Creator/MarkiePost & Florence [=LaRue=] Vs. Ed Begley, Jr. & Dack Rambo.

* WriteWhoYouKnow: The origin of the series lay in the game nights Burt Reynolds used to hold at his house; the set was modelled after his living room.

* DuelingShows: Against the Barry-Enright adaptation of ''Pictionary''.

** Several weeks of the Bert Convy version were missing in action on GSN, possibly due to celebrity clearance issues. Clips of them were shown in early GSN promos. They included Sally Struthers & Vicki Lawrence Vs. Ed Marinaro & Charles Nelson Reilly, Loni Anderson & Martha Raye Vs. Burt Reynolds & Charles Nelson Reilly, Edie [=McClurg=] & Donna Pescow Vs. Pat [=McCormick=] & Paul Williams, and Markie Post & Florence [=LaRue=] Vs. Ed Begley, Jr. & Dack Rambo.

* RetroactiveRecognition: Back in his ''Series/GrowingPains'' days, Creator/LeonardoDiCaprio was once a celebrity contestant on the teen version of ''Win, Lose, or Draw''.

** The only way to see reruns of the 2014 Disney Channel revival is on YouTube or file-sharing sites.

* KeepCirculatingTheTapes: Convy and Weller's episodes reran from 1990 to 1992 on Creator/USANetwork, and only the Convy episodes ran from 2002 to 2004 on Creator/{{GSN}}. The NBC version haven't been seen since the original run. Somewhat ironically, Creator/VH1's ''I Love the '80s'' series showed clips of the NBC version...and '''only''' the NBC version.

** Several weeks of the Bert Convy version were missing in action on GSN, possibly due to celebrity clearance issues. Clips of them were shown in early GSN promos. They included Sally Struthers & Vicki Lawrence Vs. Ed Marinaro & Charles Nelson Reilly, Charles Nelson Reilly & Burt Reynolds Vs. two unknown female celebrities, Loni Anderson & Martha Raye Vs. Burt Reynolds & Charles Nelson Reilly, Edie [=McClurg=] &and Donna Pescow Vs. Pat [=McCormick=] & Paul Williams, Markie Post & Florence [=LaRue=] Vs. Ed Begley, Jr. & Dack Rambo.

** Several weeks of the Bert Convy version were missing in action on GSN, possibly due to celebrity clearance issues. Clips of them were shown in early GSN promos. They included Sally Struthers & Vicki Lawrence Vs. Ed Marinaro & Charles Nelson Reilly, Charles Nelson Reilly & Burt Reynolds Vs. two unknown female celebrities, Loni Anderson & Martha Raye Vs. two unknown male celebrities, and Edie [=McClurg=] &and Donna Pescow Vs. Pat [=McCormick=] & Paul Williams.

** Several weeks of the Bert Convy version were missing in action on GSN, possible due to celebrity clearance issues. Clips of them were shown in early GSN promos. They included Sally Struthers & Vicki Lawrence Vs. Ed Marinaro & Charles Nelson Reilly, Charles Nelson Reilly & Burt Reynolds Vs. two unknown female celebrities, Loni Anderson & Martha Raye Vs. two unknown male celebrities, and Edie [=McClurg=] &and Donna Pescow Vs. Pat [=McCormick=] & Paul Williams.

* HeyItsThatGuy:
** Bert Convy was already known for hosting ''Series/{{Tattletales}}'' and ''Super Series/{{Password}}''.
*** His partner producer for the show, Burt Reynolds, simply needs no introduction.
** Robb Weller was an ''Series/EntertainmentTonight'' host.
** Vicki Lawrence was an actress/singer/comedienne.
** Marc Price was a regular on ''Series/FamilyTies''.
** During Vicki's illness, [[Series/AllInTheFamily Sally Struthers]] was a substitute host.
** Since the Disney Channel revival is going to have all of its stars be guest contestants, expect a lot of this. The following pairings have participated so far (all involving a co-star pairing):
*** [[Series/KickinIt Olivia Holt and Leo Howard]]
*** [[Series/LivAndMaddie Dove Cameron and Joey Bragg]]
*** [[Series/{{Jessie}} Peyton List and Cameron Boyce]]
*** [[Series/DogWithABlog G Hannelius and Blake Michael]]
*** [[Film/TeenBeachMovie Garret Clayton and Chrissie Fit]]
*** [[Series/LabRats Tyler Jackson Williams and Billy Unger]]
*** [[Series/MightyMed Bradley Steven Perry and Jake Short]] (whose episode they were in also had twins [[WebVideo/{{React}} Megan and Shannon Clemons]] make an appearance)
*** The host himself, Justin "Kredible" Willman has appeared on several magic specials and played a magician in the episode "Alaka-Scram!" on ''TheSuiteLifeOnDeck''. This isn't even the only competition show Willman currently hosts: he's also on ''Cupcake Wars'' over on Creator/FoodNetwork, and previously hosted ''Series/ScrabbleShowdown'' and ''[=HubWorld=]'' on [[Creator/DiscoveryFamily Hub Network]].
* HeyItsThatVoice:
** On the British version, the voice artist who did the voice for [[EvilSoundsDeep Zordrak]] from ''WesternAnimation/TheDreamstone'' once appeared as a contestant.
** After moving from Florida to LA, ''Teen'' was announced by Mark Wahlberg; Stone-Stanley, which co-produced that version, would soon recruit him as the first announcer for ''Series/ShopTilYouDrop'', and would later host ''Free 4 All'' on the Creator/USANetwork and ''Series/RussianRoulette''.
** On the Disney Channel revival, [[WesternAnimation/PhineasAndFerb Major Monogram and Dr. Doofenschmirtz]] and [[WesternAnimation/GravityFalls Grunkle Stan]] were guest animators (the voice actors are also their respective shows' creators).

** Several weeks of the Bert Convy version were missing in action on GSN, possible due to celebrity clearance issues. Clips of them were shown in early GSN promos. They included Sally Struthers and Vicki Lawrence vs. Ed Marinaro and Charles Nelson Reilly, Charles Nelson Reilly and Burt Reynolds with two unknown female celebrities, Loni Anderson and Martha Raye with two unknown male celebrities, and Edie [=McClurg=] and Donna Pescow vs. Pat [=McCormick=] and Paul Williams.

*** The host himself, Justin "Kredible" Willman has appeared on several magic specials and played a magician in the episode "Alaka-Scram!" on ''TheSuiteLifeOnDeck''. This isn't even the only competition show Willman currently hosts: he's also on ''Cupcake Wars'' over on Creator/FoodNetwork, and previously hosted ''Series/ScrabbleShowdown'' and '[=HubWorld=]'' on [[Creator/DiscoveryFamily Hub Network]].

*** The host himself, Justin "Kredible" Willman has appeared on several magic specials and played a magician in the episode "Alaka-Scram!" on ''TheSuiteLifeOnDeck''. This isn't even the only competition show Willman currently hosts: he's also on ''Cupcake Wars'' over on Creator/FoodNetwork, and previously hosted ''Scrabble Showdown'' on [[Creator/DiscoveryFamily Hub Network]].

** On the Disney Channel revival, [[WesternAnimation/PhineasAndFerb Major Monogram and Dr. Doofenschmirtz]] and [[Series/GravityFalls Grunkle Stan]] were guest animators (the voice actors are also their respective shows' creators).

*** The host himself, Justin "Kredible" Willman has appeared on several magic specials and played a magician in the episode "Alaka-Scram!" on ''TheSuiteLifeOnDeck''. This isn't even the only competition show Willman currently hosts: he's also on ''Cupcake Wars'' over on Creator/FoodNetwork, and previously hosted ''Scrabble Showdown'' on Creator/HubNetwork.

*** The host himself, Justin "Kredible" Willman has appeared on several magic specials and played a magician in the episode "Alaka-Scram!" on ''TheSuiteLifeOnDeck''. This isn't even the only competition show Willman currently hosts: he's also on ''Cupcake Wars'' over on Creator/FoodNetwork.