| | Opponent |
| Date | Game Results | Site | UM Coach | Game Notes | Conference | Head Coach | Nickname |
| 3/15/1990 | L 91-81 | Away | John Calipari | NIT First Round at Cole Field House. | ACC | Gary Williams | Terrapins1) |
| 12/29/1993 | W 94-80 | Home | John Calipari | UMass #9. Abdow’s Classic, Springfield, MA | ACC | Gary Williams | Terrapins |
| 3/19/1994 | L 95-87 | Neutral | John Calipari | NCAA 2nd Round, Kansas Coliseum, Park City (Wichita), KS. Midwest Region seeds: MA 2, MD 10. UMass ranked #8. Camby 32 & 10, Roe 17 & 11, but can't stop MD's 60% shooting. | ACC | Gary Williams | Terrapins |
| 12/10/1994 | W 85-74 | Away | John Calipari | UMass #5, Maryland #11. Baltimore Arena, Baltimore, MD | ACC | Gary Williams | Terrapins |
| 12/2/1995 | W 50-47 | Away | John Calipari | UMass #5, Maryland #19. Franklin National Bank Classic, USAir Arena, Landover, MD | ACC | Gary Williams | Terrapins |
| 2/15/1997 | W 78-61 | Home | Bruiser Flint | Maryland #10. At the Worcester Centrum. Clarke 22 pts, Ketner 19 & 12, Travieso 16 pts. | ACC | Gary Williams | Terrapins |