75		Semi-Pro (Comedy, Sport, 2008)
73		Bad News Bears (Comedy, Sport, 2005)
61		The Replacements (Comedy, Sport, 2000)
54		17 Again (Comedy, Drama, Family, 2009)
54		The Comebacks (Comedy, Sport, 2007)
50		Rebound (Comedy, Family, Sport, 2005)
49		The Holiday (Comedy, Romance, 2006)
49		Goon (Comedy, Sport, 2011)
49		Blades of Glory (Comedy, Sport, 2007)
48		Dodgeball: A True Underdog Story (Comedy, Sport, 2004)
48		Napoleon Dynamite (Comedy, 2004)
47		Back to School (Comedy, Romance, Sport, 1986)
47		Just Wright (Comedy, Romance, Sport, 2010)
46		Bring It On (Comedy, Sport, 2000)
46		Stick It (Comedy, Drama, Sport, 2006)
46		Rushmore (Comedy, Drama, 1998)
46		The Game Plan (Comedy, Family, Sport, 2007)
46		Win Win (Comedy, Drama, Sport, 2011)
46		She's the Man (Comedy, Romance, Sport, 2006)
46		Playing for Keeps (Comedy, Romance, Sport, 2012)
45		Major League (Comedy, Sport, 1989)
45		Grown Ups (Comedy, 2010)
45		In & Out (Comedy, Romance, 1997)
45		BASEketball (Comedy, Sport, 1998)
45		Diary of a Wimpy Kid (Comedy, Family, 2010)
45		The Waterboy (Comedy, Sport, 1998)
44		Project X (Comedy, Crime, 2012)
44		Ted (Comedy, Fantasy, 2012)
44		Juno (Comedy, Drama, 2007)
44		The Three Stooges (Comedy, 2012)
44		Meet Bill (Comedy, Drama, 2007)
43		The Ringer (Comedy, Sport, 2005)
43		Laggies (Comedy, Romance, 2014)
43		Grudge Match (Comedy, Sport, 2013)
42		Little Giants (Comedy, Family, Sport, 1994)
41		Dazed and Confused (Comedy, 1993)
41		Dope (Comedy, Crime, Drama, 2015)
41		Ready to Rumble (Comedy, Sport, 2000)
41		Ghost World (Comedy, Drama, 2001)
41		Kick-Ass (Action, Comedy, 2010)
41		The Benchwarmers (Comedy, Romance, Sport, 2006)
41		Out Cold (Comedy, Sport, 2001)
40		Major League II (Comedy, Sport, 1994)
40		Hamlet 2 (Comedy, Music, 2008)
40		Just One of the Guys (Comedy, Romance, 1985)
40		Kingpin (Comedy, Sport, 1996)
40		Step Brothers (Comedy, 2008)
40		College (Comedy, 2008)
40		Happy Gilmore (Comedy, Sport, 1996)
40		Drillbit Taylor (Comedy, Drama, 2008)
40		Teen Wolf (Comedy, Fantasy, 1985)
40		Fired Up! (Comedy, 2009)
39		Young Adult (Comedy, Drama, 2011)
39		Trailer Park Boys: The Movie (Comedy, Crime, 2006)
39		Prom (Comedy, Drama, 2011)
38		Me and Earl and the Dying Girl (Comedy, Drama, 2015)
38		Charlie Bartlett (Comedy, Drama, Romance, 2007)
38		Nancy Drew (Comedy, Crime, Family, 2007)
38		Just Friends (Comedy, Romance, 2005)
38		The To Do List (Comedy, Romance, 2013)
37		The Ice Harvest (Comedy, Crime, Drama, 2005)
36		Bend It Like Beckham (Comedy, Drama, Romance, 2002)
36		Get Over It (Comedy, Romance, 2001)
36		Ferris Bueller's Day Off (Comedy, Romance, 1986)
36		Here Comes the Boom (Action, Comedy, Sport, 2012)
35		What Happens in Vegas (Comedy, Romance, 2008)
35		She's All That (Comedy, Romance, 1999)
35		Dance of the Dead (Comedy, Horror, 2008)
35		Superbad (Comedy, 2007)
35		Choke (Comedy, Drama, 2008)
35		Harold & Kumar Escape from Guantanamo Bay (Adventure, Comedy, 2008)
35		Kindergarten Cop (Comedy, 1990)
35		Fast Times at Ridgemont High (Comedy, Drama, 1982)
35		Cabin Fever 2: Spring Fever (Comedy, Horror, 2009)
35		The Longest Yard (Comedy, Crime, Sport, 2005)
35		Valley Girl (Comedy, Romance, 1983)
35		Hot Tub Time Machine (Comedy, Sci-Fi, 2010)
35		Easy A (Comedy, Romance, 2010)
35		The Brady Bunch Movie (Comedy, 1995)
35		Clueless (Comedy, Romance, 1995)
35		World's Greatest Dad (Comedy, Drama, 2009)
35		Hotel for Dogs (Comedy, Family, 2009)
34		Drive Me Crazy (Comedy, Drama, Romance, 1999)
34		Seven Psychopaths (Comedy, Crime, 2012)
34		The Sitter (Comedy, 2011)
34		Election (Comedy, Drama, Romance, 1999)
34		Accepted (Comedy, 2006)
34		College Road Trip (Adventure, Comedy, Drama, 2008)
34		Fame (Comedy, Drama, Musical, 2009)
34		TiMER (Comedy, Drama, Fantasy, 2009)
34		Rocket Science (Comedy, Drama, 2007)
34		Space Jam (Animation, Adventure, Comedy, 1996)
34		The Ref (Comedy, Crime, Drama, 1994)
33		Better Living Through Chemistry (Comedy, Drama, 2014)
33		The Chumscrubber (Comedy, Drama, 2005)
33		Teeth (Comedy, Fantasy, Horror, 2007)
33		In a World... (Comedy, 2013)
33		Mean Girls (Comedy, 2004)
33		Sex Tape (Comedy, Romance, 2014)
33		Dan in Real Life (Comedy, Drama, Romance, 2007)
33		Adult World (Comedy, Drama, 2013)
33		We're the Millers (Comedy, Crime, 2013)
33		Men, Women & Children (Comedy, Drama, 2014)
32		Ice Princess (Comedy, Drama, Family, 2005)
32		A Christmas Story (Comedy, Family, 1983)
32		13 Going on 30 (Comedy, Fantasy, Romance, 2004)
32		Anger Management (Comedy, 2003)
32		Welcome to Collinwood (Comedy, Crime, 2002)
32		American Wedding (Comedy, Romance, 2003)
32		Tokyo Godfathers (Animation, Adventure, Comedy, 2003)
32		Hot Tub Time Machine 2 (Comedy, Sci-Fi, 2015)
32		The Night Before (Comedy, 2015)
32		The Girl Next Door (Comedy, Drama, Romance, 2004)
32		White Men Can't Jump (Comedy, Drama, Sport, 1992)
32		Yours, Mine & Ours (Comedy, Family, Fantasy, 2005)
32		A League of Their Own (Comedy, Drama, Sport, 1992)
32		Despicable Me 2 (Animation, Adventure, Comedy, 2013)
31		Run, Fatboy, Run (Comedy, Romance, Sport, 2007)
31		Wet Hot American Summer (Comedy, Romance, 2001)
31		Mr. Woodcock (Comedy, Romance, Sport, 2007)
31		Balls of Fury (Comedy, Crime, Sport, 2007)
31		Talladega Nights: The Ballad of Ricky Bobby (Action, Comedy, Sport, 2006)
31		National Lampoon's Christmas Vacation (Comedy, Family, 1989)
31		Chalet Girl (Comedy, Romance, Sport, 2011)
31		Back to the Future (Adventure, Comedy, Sci-Fi, 1985)
31		Eight Crazy Nights (Animation, Comedy, Musical, 2002)
31		Nacho Libre (Comedy, Family, Sport, 2006)
31		Trainwreck (Comedy, Drama, Romance, 2015)
31		Planes, Trains & Automobiles (Comedy, Drama, 1987)
31		Barely Lethal (Action, Adventure, Comedy, 2015)
30		Detroit Rock City (Comedy, Music, 1999)
30		Wimbledon (Comedy, Romance, Sport, 2004)
30		The Princess Diaries (Comedy, Family, Romance, 2001)
30		Postcards from the Edge (Comedy, Drama, 1990)
30		Romy and Michele's High School Reunion (Comedy, 1997)
30		Home Alone (Comedy, Family, 1990)
30		Cuban Fury (Comedy, Romance, Sport, 2014)
30		Billy Madison (Comedy, 1995)
30		Trees Lounge (Comedy, Drama, 1996)
30		Anywhere But Here (Comedy, Drama, 1999)
30		Encino Man (Comedy, 1992)
30		American Pie (Comedy, 1999)
29		Lymelife (Comedy, Drama, Romance, 2008)
29		Never Been Kissed (Comedy, Drama, Romance, 1999)
29		Pump Up the Volume (Comedy, Drama, Music, 1990)
29		The Mighty Ducks (Comedy, Drama, Family, 1992)
29		Smart People (Comedy, Drama, Romance, 2008)
29		10 Things I Hate About You (Comedy, Drama, Romance, 1999)
29		Wild Child (Comedy, Drama, Romance, 2008)
29		Bachelorette (Comedy, Romance, 2012)
29		Grosse Pointe Blank (Action, Comedy, Crime, 1997)
29		The Santa Clause (Comedy, Drama, Family, 1994)
29		A Very Harold & Kumar 3D Christmas (Adventure, Comedy, 2011)
29		Think Like a Man (Comedy, Romance, 2012)
29		Pirate Radio (Comedy, Drama, Music, 2009)
29		Happy-Go-Lucky (Comedy, Drama, Romance, 2008)
29		Struck by Lightning (Comedy, Drama, 2012)
29		Superman III (Action, Comedy, Sci-Fi, 1983)
29		Can't Buy Me Love (Comedy, Drama, Romance, 1987)
29		John Tucker Must Die (Comedy, Romance, 2006)
29		Grind (Adventure, Comedy, Sport, 2003)
29		It's Kind of a Funny Story (Comedy, Drama, Romance, 2010)
29		Varsity Blues (Comedy, Drama, Romance, 1999)
29		Love and Other Disasters (Comedy, Romance, 2006)
29		Simon Birch (Comedy, Drama, Family, 1998)
29		Corrina, Corrina (Comedy, Drama, Romance, 1994)
29		Peggy Sue Got Married (Comedy, Drama, Fantasy, 1986)
29		High School Musical 3: Senior Year (Comedy, Drama, Family, 2008)
28		The Best Man Holiday (Comedy, Drama, 2013)
28		The Perfect Score (Comedy, Crime, 2004)
28		My Super Ex-Girlfriend (Comedy, Romance, Sci-Fi, 2006)
28		Click (Comedy, Drama, Fantasy, 2006)
28		Detention (Comedy, Horror, Sci-Fi, 2011)
28		Top Five (Comedy, Romance, 2014)
28		Aquamarine (Comedy, Family, Fantasy, 2006)
28		Starter for 10 (Comedy, Drama, Romance, 2006)
28		Celeste & Jesse Forever (Comedy, Drama, Romance, 2012)
28		Arthur Christmas (Animation, Adventure, Comedy, 2011)
28		Footloose (Comedy, Drama, Music, 2011)
28		LOL (Comedy, Drama, Romance, 2012)
28		Hotel Transylvania (Animation, Comedy, Family, 2012)
27		Dil Chahta Hai (Comedy, Drama, Romance, 2001)
27		The Life Aquatic with Steve Zissou (Adventure, Comedy, Drama, 2004)
27		The Hitchhiker's Guide to the Galaxy (Adventure, Comedy, Sci-Fi, 2005)
27		Mother's Day (Comedy, Drama, 2016)
27		Escape from Planet Earth (Animation, Adventure, Comedy, 2013)
27		RED 2 (Action, Comedy, Crime, 2013)
27		How to Be Single (Comedy, Romance, 2016)
27		Sisters (Comedy, 2015)
27		The Spectacular Now (Comedy, Drama, Romance, 2013)
27		The DUFF (Comedy, 2015)
27		The Family Stone (Comedy, Drama, Romance, 2005)
27		Play It to the Bone (Comedy, Drama, Sport, 1999)
27		Bull Durham (Comedy, Romance, Sport, 1988)
27		Life or Something Like It (Comedy, Romance, 2002)
27		Mystery, Alaska (Comedy, Drama, Sport, 1999)
27		The New Guy (Comedy, 2002)
27		Saving Mr. Banks (Biography, Comedy, Drama, 2013)
27		3 Idiots (Comedy, Drama, 2009)
27		Tangerine (Comedy, Drama, 2015)
27		Caddyshack (Comedy, Romance, Sport, 1980)
27		The Hot Chick (Comedy, Fantasy, 2002)
27		The Cannonball Run (Action, Comedy, Sport, 1981)

Notes: Movies similar to The Winning Season, Movies like The Winning Season, Comedy, Sport, James C. Strouse, Sam Rockwell, Emma Roberts, Rob Corddry, Emily Rios, Films, Video, Movie Similarities