| 21.3.1959 | 12 h Sebring | 42 | Alfa Romeo Giulietta Veloce | Rubin / Grossman / Comito | Robert Grossman | 42nd |
| 12.4.1959 | SCCA Regional Vineland [GP+HP] | 99 | Alfa Romeo Giulietta Veloce | Bob Grossman | | 2nd |
| 12.4.1959 | SCCA Regional Vineland [GP+HP] | 99 | Alfa Romeo Giulietta Veloce | Bob Grossman | | DNA |
| 12.4.1959 | SCCA Regional Vineland [FP+GP] | 99 | Alfa Romeo Giulietta Veloce | Bob Grossman | | DNA |
| 19.4.1959 | SCCA National Marlboro [FP+GP] | 90 | Alfa Romeo Giulietta Veloce | Bob Grossman | | 10th |
| 26.4.1959 | SCCA Regional Lime Rock [P4] | 9 | Alfa Romeo Giulietta Veloce | Bob Grossman | | 4th |
| 3.5.1959 | SCCA National Virginia [FP+GP+HP+IP+JP+HM] | 9 | Alfa Romeo Giulietta Spider Veloce | Bob Grossman | | 9th |
| 3.5.1959 | SCCA National Virginia [BP+CP+DP+EP] | 19 | Ferrari 250 GT | Bob Grossman | | 4th |
| 9.5.1959 | SCCA Regional Lime Rock [P4] | 9 | Alfa Romeo Giulietta Veloce | Bob Grossman | | 3rd |
| 9.5.1959 | SCCA Regional Lime Rock [BM+CM+DM+EM+FM] | 22 | Ferrari 250 GT | Bob Grossman | | 7th |
| 17.5.1959 | SCCA National Cumberland [GP] | 9 | Alfa Romeo Giulietta Veloce | Bob Grossman | | 1st |
| 17.5.1959 | SCCA National Cumberland [BP+CP+DP] | 29 | Ferrari 250 GT | Bob Grossman | | 3rd |
| 30.5.1959 | SCCA National Bridgehampton [GP] | 91 | Alfa Romeo Giulietta Veloce | Bob Grossman | | 5th |
| 31.5.1959 | SCCA National Bridgehampton [BP+CP+DP+EP] | 9 | Ferrari 250 GT | Bob Grossman | | 2nd |
| 21.6.1959 | 24 h Le Mans | 16 | Ferrari 250 GT | Grossman / Tavano | North American Racing Team | 5th |
| 4.7.1959 | SCCA National Lime Rock [BP+CP+DP] | 9 | Ferrari 250 GT | Bob Grossman | | 1st |
| 9.8.1959 | SCCA National Montgomery [BP+CP+DP] | 19 | Ferrari 250 GT | Bob Grossman | | 1st |
| 9.8.1959 | SCCA National Montgomery [GP+HP+IP] | 97 | Alfa Romeo Giulietta Spider Veloce | Bob Grossman | | 7th |
| 15.8.1959 | 8 h Lime Rock | 27 | Saab | Grossman / Constantine | | 8th |
| 6.9.1959 | Preliminary Thompson [CM+DM+EM+FM] | 91 | Ferrari 250 GT | Bob Grossman | | 9th |
| 7.9.1959 | SCCA National Thompson [CM+DM+EM+FM] | 91 | Ferrari 250 GT | Bob Grossman | | 6th |
| 7.9.1959 | SCCA National Thompson [GM+HM+GP+HP+IP] | 145 | Turner | Bob Grossman | | 24th |
| 12.9.1959 | SCCA National Road America [BP+CP+DP+EP+FP] | 2 | Ferrari 250 GT | Bob Grossman | Robert Grossman | DNA |
| 12.9.1959 | LISCA Lime Rock [Class 10+11+12] | 9 | Ferrari 250 GT | Bob Grossman | | ?th |
| 20.9.1959 | SCCA Interclub Bridgehampton [Production +1.6] | 119 | Ferrari 250 GT | Bob Grossman | | 1st |
| 26.9.1959 | GP Watkins Glen | 95 | Ferrari 250 GT | Bob Grossman | Robert M. Grossman | DNF |
| 26.9.1959 | SCCA National Watkins Glen [BP+CP+DP] | 96 | Jaguar XK150 | Bob Grossman | Robert M. Grossman | DNA |
| 17.10.1959 | SCCA Regional Lime Rock [Main] | 9 | Jaguar C-type | Bob Grossman | | DNA |
| 4.12.1959 | Governor's Trophy [S+2.0] | 18 | Ferrari 250 GT | Bob Grossman | | 9th |
| 4.12.1959 | Preliminary Governor's Trophy [S+2.0] | 18 | Ferrari 250 GT | Bob Grossman | | 19th |
| 5.12.1959 | Nassau [Ferrari] | 18 | Ferrari 250 GT | Bob Grossman | | 7th |
| 6.12.1959 | Nassau Memorial Trophy | 18 | Ferrari 250 GT | Bob Grossman | | 1st |
| 6.12.1959 | Nassau Trophy | 18 | Ferrari 250 GT | Bob Grossman | | 19th |