| Peak | Song | Entered | Wks | Annual |
|---|---|---|---|---|
| 1 | Into the Groove | 18 Aug 1985 | 10 | 1985 #5 |
| 1 | Dress You Up | 20 Oct 1985 | 9 | 1985 #20 |
| 1 | Papa Don't Preach | 20 Jul 1986 | 10 | 1986 #3 |
| 1 | Open Your Heart | 28 Dec 1986 | 9 | 1987 #12 |
| 1 | La isla bonita | 12 Apr 1987 | 8 | 1987 #1 |
| 1 | Who's That Girl | 2 Aug 1987 | 10 | 1987 #7 |
| 1 | Like a Prayer | 26 Mar 1989 | 8 | 1989 #2 |
| 1 | Vogue | 13 May 1990 | 9 | 1990 #3 |
| 1 | Justify My Love | 25 Nov 1990 | 8 | – |
| 1 | Rescue Me | 3 Mar 1991 | 6 | – |
| 1 | You'll See | 14 Nov 1995 | 8 | 1995 #3 |
| 1 | Don't Cry for Me Argentina | 7 Jan 1997 | 7 | – |
| 2 | Like a Virgin | 30 Dec 1984 | 9 | 1985 #11 |
| 2 | Live to Tell | 11 May 1986 | 8 | – |
| 2 | True Blue | 26 Oct 1986 | 8 | 1986 #5 |
| 2 | Express Yourself | 11 Jun 1989 | 8 | 1989 #19 |
| 2 | Cherish | 10 Sep 1989 | 4 | – |
| 3 | Dear Jessie | 4 Feb 1990 | 7 | – |
| 3 | Deeper and Deeper | 8 Dec 1992 | 8 | – |
| 3 | Rain | 3 Aug 1993 | 6 | 1993 #21 |
| 4 | Material Girl | 17 Mar 1985 | 9 | 1985 #27 |
| 4 | Secret | 11 Oct 1994 | 7 | 1994 #11 |
| 4 | Oh Father | 23 Jan 1996 | 5 | – |
| 5 | Gambler | 24 Nov 1985 | 6 | – |
| 5 | The Look of Love | 27 Dec 1987 | 6 | – |
| 5 | Hanky Panky | 29 Jul 1990 | 5 | 1966 #9, 1990 #22 |
| 5 | Erotica | 20 Oct 1992 | 6 | – |
| 5 | I'll Remember | 12 Apr 1994 | 6 | – |
| 5 | You Must Love Me | 4 Nov 1996 | 6 | 1996 #43 |
| 7 | Causing a Commotion | 4 Oct 1987 | 4 | 1987 #25 |
| 7 | Bad Girl | 16 Mar 1993 | 5 | – |
| 8 | Bye Bye Baby | 4 Jan 1994 | 5 | – |
| 8 | One More Chance | 2 Apr 1996 | 4 | – |
| 11 | Another Suitcase in Another Hall | 1 Apr 1997 | 3 | – |
| 12 | This Used to Be My Playground | 14 Jul 1992 | 6 | – |
| 13 | Holiday | 6 Feb 1984 | 6 | – |
| 14 | Angel | 16 Jun 1985 | 5 | – |
| 15 | Bedtime Story | 7 Mar 1995 | 4 | – |
| 17 | Fever | 7 Apr 1993 | 4 | – |
| 17 | Human Nature | 25 Jul 1995 | 6 | – |
| 18 | Keep It Together | 1 Apr 1990 | 3 | – |
| 20 | Crazy for You | 5 May 1985 | 2 | – |
| 22 | Take a Bow | 27 Dec 1994 | 2 | 1995 #28 |
| 25 | Borderline | 22 Jul 1984 | 1 | – |
| 26 | Oh Father | 21 Jan 1990 | 2 | – |
| 29 | Lucky Star | 15 Apr 1984 | 1 | – |