| First Team | Second Team Matches | Youth Matches | League debuts | Associated with both clubs | Transfers | Programmes |
| Seasons | Competition | Date | Venue | Results | Wolves Manager | Barnsley Manager | |
| 1990/91 | Football League (2) | 24 November 1990 | Oakwell Ground | D | 1-1 | Graham Turner | Mel Machin |
| 1990/91 | Football League (2) | 9 March 1991 | Molineux | L | 0-5 | Graham Turner | Mel Machin |
| 1991/92 | Football League (2) | 5 October 1991 | Molineux | L | 1-2 | Graham Turner | Mel Machin |
| 1991/92 | Football League (2) | 25 April 1992 | Oakwell Ground | L | 0-2 | Graham Turner | Mel Machin |
| 1992/93 | Football League (N1) | 1 September 1992 | Oakwell Ground | W | 1-0 | Graham Turner | Mel Machin |
| 1992/93 | Football League (N1) | 27 January 1993 | Molineux | W | 1-0 | Graham Turner | Mel Machin |
| 1993/94 | Football League (N1) | 13 November 1993 | Molineux | D | 1-1 | Graham Turner | Viv Anderson |
| 1993/94 | Football League (N1) | 30 April 1994 | Oakwell Ground | L | 0-2 | Graham Taylor | Viv Anderson |
| 1994/95 | Football League (N1) | 31 December 1994 | Oakwell Ground | W | 3-1 | Graham Taylor | Danny Wilson |
| 1994/95 | Football League (N1) | 8 April 1995 | Molineux | D | 0-0 | Graham Taylor | Danny Wilson |
| 1995/96 | Football League (N1) | 4 November 1995 | Oakwell Ground | L | 0-1 | Graham Taylor | Danny Wilson |
| 1995/96 | Football League (N1) | 8 April 1996 | Molineux | D | 2-2 | Mark McGhee | Danny Wilson |
| 1996/97 | Football League (N1) | 2 November 1996 | Molineux | D | 3-3 | Mark McGhee | Danny Wilson |
| 1996/97 | Football League (N1) | 22 February 1997 | Oakwell Ground | W | 3-1 | Mark McGhee | Danny Wilson |
| 1998/99 | Football League (N1) | 31 October 1998 | Molineux | D | 1-1 | Mark McGhee | John Hendrie |
| 1998/99 | Football League (N1) | 20 March 1999 | Oakwell Ground | W | 3-2 | Colin Lee | John Hendrie |
| 1999/00 | Football League (N1) | 16 October 1999 | Oakwell Ground | W | 2-1 | Colin Lee | Dave Bassett |
| 1999/00 | Football League (N1) | 22 April 2000 | Molineux | W | 2-0 | Colin Lee | Dave Bassett |
| 2000/01 | Football League (N1) | 24 October 2000 | Oakwell Ground | W | 2-1 | Colin Lee | Dave Bassett |
| 2000/01 | Football League (N1) | 2 December 2000 | Molineux | W | 2-0 | Colin Lee | Dave Bassett |
| 2001/02 | Football League (N1) | 27 November 2001 | Molineux | W | 4-1 | Dave Jones | Steve Parkin |
| 2001/02 | Football League (N1) | 29 January 2002 | Oakwell Ground | L | 0-1 | Dave Jones | Steve Parkin |
| 2006/07 | Football League (C) | 16 September 2006 | Oakwell Ground | L | 0-1 | Mick McCarthy | Andy Ritchie |
| 2006/07 | Football League (C) | 1 January 2007 | Molineux | W | 2-0 | Mick McCarthy | Simon Davey |
| 2007/08 | Football League (C) | 10 November 2007 | Molineux | W | 1-0 | Mick McCarthy | Simon Davey |
| 2007/08 | Football League (C) | 4 December 2007 | Oakwell Ground | L | 0-1 | Mick McCarthy | Simon Davey |
| 2008/09 | Football League (C) | 13 December 2008 | Molineux | W | 2-0 | Mick McCarthy | Simon Davey |
| 2008/09 | Football League (C) | 25 April 2009 | Oakwell Ground | D | 1-1 | Mick McCarthy | Simon Davey |
| 2012/13 | Football League (C) | 21 August 2012 | Molineux | W | 3-1 | Stole Solbakken | Keith Hill |
| 2012/13 | Football League (C) | 15 February 2013 | Oakwell Ground | L | 1-2 | Dean Saunders | David Flitcroft |
| 2013/14 | Friendly | 20 July 2013 | Oakwell Ground | D | 2-2 | Kenny Jackett | David Flitcroft |
| 2016/17 | Football League (C) | 13 September 2016 | Molineux | L | 0-4 | Walter Zenga | Paul Heckingbottom |
| 2016/17 | Football League (C) | 31 January 2017 | Oakwell Ground | W | 3-1 | Paul Lambert | Paul Heckingbottom |
| 2017/18 | Football League (C) | 23 September 2017 | Molineux | W | 2-1 | Nuno Espirito Santo | Paul Heckingbottom |
| 2017/18 | Football League (C) | 13 January 2018 | Oakwell Ground | D | 0-0 | Nuno Espirito Santo | Paul Heckingbottom |
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