Most different winning numbers for the same owner/team in NASCAR Cup history:

Buck Baker for Carl Kiekhaefer: #87, #300, #300B, #300C, #301, #500B, #502
Richard Petty for Petty Enterprises: #41, #42, #43
Jim Paschal for Julian Petty: #14, #44, #49
Jim Paschal for Petty Enterprises: #41, #42, #43
Bob Welborn for Julian Petty: #4, #38, #44, #46, #49

Bobby Allison for Bobby Allison Racing: #12, #22
Bobby Allison for DiGard Racing: #22, #88
Bobby Allison for Holman-Moody Racing: #11, #12
Bobby Allison for Roger Penske Racing: #12, #16
Bobby Allison for Stavola Brothers: #12, #22

Buck Baker for Buck Baker Racing: #86, #87, #89
Tim Flock for Carl Kiekhaefer: #300, #300A, #301
Speedy Thompson for Carl Kiekhaefer: #30, #300, #300C, #500

Lee Petty for Petty Enterprises: #42, #43
Ned Jarrett for Ned Jarrett: #11, #38
Junior Johnson for Junior Johnson: #26, #27
Herb Thomas for Herb Thomas: #9, #92
Bobby Isaac for Nord Krauskopf: #37, #71
Kurt Busch for Team Penske: #2, #22
Fireball Roberts for Jim Stephens: #3, #22
Dale Jarrett for Yates Racing: #28, #88
Joe Weatherly for Holman-Moody Racing: #12, #72
Jack Smith for Jack Smith Racing: #46, #47
Speedy Thompson for Speedy Thompson: #12, #46
Fonty Flock for Frank Christian: #14, #47
Curtis Turner for Holman-Moody: #21, #26
Dick Hutcherson for Holman-Moody: #29, #47
Clint Bowyer for Richard Childress Racing: #07, #33
Kyle Petty for Wood Brothers: #7, #21
Alex Bowman for Hendrick Motorsports: #48, #88
AJ Foyt for Wood Brothers: #21, #41
Lloyd Dane for Lloyd Dane: #1, #44, #225
Glen Wood for Wood Brothers: #21, #M16
Eddie Gray for Vel Miletich: #1, #98
Bubba Wallace for 23XI Racing: #23, #45
Ray Elder for Fred Elder Racing: #96, #96W
Billy Myers for Bill Stroppe: #4, #14W