| Various Artists
The Best Of Mountain Stage Volume 1
07: Jesse Winchester - Songbird
| | Blue Plate Music USA | BPM-001CD | 1991 | CD Album | 0 | | |
| Various Artists
The Best Of Mountain Stage Live Volume 1
07: Jesse Winchester - Songbird
| | This Way Up Europe | 514 494-2 | 1993 | CD Album | 0 | | |
| Various Artists
20 Years Of Stony Plain
1-09: Jesse Winchester - Brand New Tennessee Waltz
| | Stony Plain Canada | SPCD 1230 | 1996 | Double CD | 0 | | |
| Various Artists
Bearsville Box
1-07: Jesse Winchester - The Brand New Tennessee Waltz 1-08: Jesse Winchester - Biloxi 2-10: Jesse Winchester - Isn't That So? 2-11: Jesse Winchester - Payday [Live Version] 2-12: Jesse Winchester - Rhumba Man [Live Version] 2-13: Jesse Winchester - Yankee Lady [Live Version]
| | Bearsville Japan | PCCY-0909 | 20 Sep 1996 | CD Box Set | 0 | | |
| Various Artists
Unconditionally Guaranteed 4
02: Jesse Winchester - Mississippi You're On My Mind
| | Uncut [Magazine] UK | UNCUT UG-5 11 | May 1999 | CD Album | 0 | 6.1 | |
| Various Artists
Meridian 1970
14: Jesse Winchester - Biloxi
| | Forever Heavenly UK | FHVN2LP CD | Feb 2005 | CD Album | 0 | | |
| Various Artists
Sugar Hill Records: A Retrospective
4-12: Jesse Winchester - Club Manhattan
| | Sugar Hill USA | SUG-CD-3999 | 2006 | CD Box Set | 0 | | |
| Various Artists
The Wire: And All The Pieces Matter -- Five Years Of Music From The Wire
13: Jesse Winchester - Step By Step
| | Nonesuch USA | 369796-2 | 2008 | CD Album | 1 | 8.1 | |
| Various Artists
Charlie Gillett's Radio Picks - Honky Tonk
01: Jesse Winchester - How Far The Horizon
| | Ace UK | CDCHD 1242 | 2 Nov 2009 | CD Album | 0 | | |
| Various Artists
Bearsville Box
1-07: Jesse Winchester - The Brand New Tennessee Waltz 1-08: Jesse Winchester - Biloxi 2-10: Jesse Winchester - Isn't That So? 2-11: Jesse Winchester - Payday [Live Version] 2-12: Jesse Winchester - Rhumba Man [Live Version] 2-13: Jesse Winchester - Yankee Lady [Live Version]
| | Bearsville Japan | VICP-70131~4 | 16 Dec 2009 | CD Box Set | 1 | | |
| Various Artists
Theme Time Radio Hour - Season 3 With Your Host Bob Dylan
1-03: Jesse Winchester - Payday
| | Ace UK | CDCH2 1270 | 2010 | Double CD | 1 | | |
| Various Artists
Blue Highways - The Ultimate Americana Music Fest 2011
07: Jesse Winchester - It's A Shame About Him
| | CRS Netherlands | CRSCD 1011 | Apr 2011 | CD Album | 0 | | |
| Various Artists
Eclipsed - 15 Tracks Of The Best New Music
01: Jesse Winchester - Ghosts
| | Uncut [Magazine] UK | UNCUT 2014 11 | Nov 2014 | CD Album | 0 | | |
| Little Feat
Little Feat & Friends
04: Jesse Winchester - Rhumba Man
| | Air Cuts Bootleg | ACCD7019 | 2015 | CD Album | 0 | | |
| Various Artists
Truckers, Kickers, Cowboy Angels, Vol 3 (1970)
1-05: Jesse Winchester - Biloxi 2-16: Jesse Winchester - Snow
| | Bear Family Germany | BCD 17363 | 2015 | Double CD | 0 | | |
| Various Artists
Truckers, Kickers, Cowboy Angels, Vol. 7 (1974-1975)
2-15: Jesse Winchester - Mississippi, You're On My Mind
| | Bear Family Germany | BCD 17367 | 2015 | Double CD | 0 | | |
| Various Artists
Mojo Presents Costello, A Collection Of Unfaithful Music
13: Jesse Winchester - Ghosts
| | Mojo [Magazine] UK | | Dec 2015 | CD Album | 0 | 7.9 | |
| Various Artists
David Hepworth Deep 70s (Underrated Cuts From A Misunderstood Decade)
Young Americans 1-01: Jesse Winchester - Payday
| | Edsel UK | EDSL0071 | 2022 | CD Box Set | 0 | | |