16‑Nov‑2009 | Champaign CH | Hard | R16 | 463 | 415 | (Q)Bjorn Rehnquist [SWE] d. (WC)Monroe | 7-6(3) 6-4 | | | | | | | | | |
16‑Nov‑2009 | Champaign CH | Hard | R32 | 463 | 189 | (WC)Monroe d. Ilija Bozoljac [SRB] | 7-6(3) 4-6 6-1 | | | | | | | | | |
19‑Oct‑2009 | USA F26 | Hard | SF | 479 | 455 | (5)Bruno Rodriguez [MEX] d. (8)Monroe | 6-1 6-4 | | | | | | | | | |
19‑Oct‑2009 | USA F26 | Hard | QF | 479 | 446 | (8)Monroe d. (4)Eric Nunez [USA] | 6-3 5-7 6-4 | | | | | | | | | |
19‑Oct‑2009 | USA F26 | Hard | R16 | 479 | 832 | (8)Monroe d. Luis Diaz Barriga [MEX] | 6-1 6-3 | | | | | | | | | |
19‑Oct‑2009 | USA F26 | Hard | R32 | 479 | 1529 | (8)Monroe d. (WC)Raymond Sarmiento [USA] | 7-6(0) 6-4 | | | | | | | | | |
12‑Oct‑2009 | USA F25 | Hard | R16 | 482 | | (WC)Dimitar Kutrovsky [BUL] d. (5)Monroe | 6-4 5-7 6-0 | | | | | | | | | |
12‑Oct‑2009 | USA F25 | Hard | R32 | 482 | 1216 | (5)Monroe d. (LL)Raphael Shiikuma Pfister [BRA] | 6-2 6-1 | | | | | | | | | |
28‑Sep‑2009 | USA F24 | Hard | R32 | 492 | 574 | Ryan Harrison [USA] d. (6)Monroe | 6-3 6-3 | | | | | | | | | |
21‑Sep‑2009 | USA F23 | Hard | QF | 496 | 683 | Blake Strode [USA] d. (7)Monroe | 6-1 6-3 | | | | | | | | | |
21‑Sep‑2009 | USA F23 | Hard | R16 | 496 | 816 | (7)Monroe d. (Q)Erling Tveit [NOR] | 6-3 6-3 | | | | | | | | | |
21‑Sep‑2009 | USA F23 | Hard | R32 | 496 | 1714 | (7)Monroe d. (Q)Tyler Hochwalt [USA] | 6-0 6-0 | | | | | | | | | |
20‑Jul‑2009 | Lexington CH | Hard | R32 | 474 | 250 | Nick Lindahl [AUS] d. Monroe | 6-1 6-2 | | | | | | | | | |
22‑Jun‑2009 | USA F14 | Hard | R16 | 394 | 981 | Ryan Harrison [USA] d. (6)Monroe | 6-2 6-4 | | | | | | | | | |
22‑Jun‑2009 | USA F14 | Hard | R32 | 394 | 789 | (6)Monroe d. Nima Roshan [AUS] | 6-4 6-3 | | | | | | | | | |
15‑Jun‑2009 | USA F13 | Hard | R16 | 401 | 272 | (2)Carlos Salamanca [COL] d. Monroe | 6-3 6-3 | | | | | | | | | |
15‑Jun‑2009 | USA F13 | Hard | R32 | 401 | 1279 | Monroe d. (WC)Conor Pollock [USA] | 6-4 6-0 | | | | | | | | | |
8‑Jun‑2009 | USA F12 | Hard | R16 | 404 | 533 | (Q)Tim Smyczek [USA] d. (7)Monroe | 2-6 7-5 6-4 | | | | | | | | | |
8‑Jun‑2009 | USA F12 | Hard | R32 | 404 | 490 | (7)Monroe d. Luis Manuel Flores [MEX] | 6-2 6-2 | | | | | | | | | |
1‑Jun‑2009 | Yuba City CH | Hard | R16 | 388 | 237 | Michael Yani [USA] d. Monroe | 6-4 6-0 | | | | | | | | | |
1‑Jun‑2009 | Yuba City CH | Hard | R32 | 388 | 218 | Monroe d. (8)Todd Widom [USA] | 7-6(4) 6-3 | | | | | | | | | |
25‑May‑2009 | Carson2 CH | Hard | R16 | 388 | 384 | (Q)Jesse Witten [USA] d. Monroe | 7-6(7) 7-6(3) | | | | | | | | | |
25‑May‑2009 | Carson2 CH | Hard | R32 | 388 | 156 | Monroe d. (3)Alex Bogomolov Jr [RUS] | 6-3 4-6 6-4 | | | | | | | | | |
4‑May‑2009 | Savannah CH | Clay | R32 | 328 | 567 | (Q)Chris Klingemann [CAN] d. Monroe | 6-2 5-7 6-4 | | | | | | | | | |
27‑Apr‑2009 | Mexico F3 | Hard | R16 | 292 | 692 | Bruno Rodriguez [MEX] d. (2)Monroe | 6-2 6-2 | | | | | | | | | |
27‑Apr‑2009 | Mexico F3 | Hard | R32 | 292 | 815 | (2)Monroe d. Adil Shamasdin [CAN] | 6-2 1-6 7-6(13) | | | | | | | | | |
6‑Apr‑2009 | Baton Rouge CH | Hard | R32 | 284 | 261 | Matthias Bachinger [GER] d. Monroe | 6-3 4-6 6-4 | | | | | | | | | |
23‑Mar‑2009 | Sarajevo CH | Hard | R32 | 286 | 278 | (8)Blaz Kavcic [SLO] d. Monroe | 3-6 7-6(4) 7-6(6) | | | | | | | | | |
16‑Mar‑2009 | Great Britain F4 | Hard | R32 | 291 | 569 | (Q)Scott Oudsema [USA] d. (5)Monroe | 6-2 6-3 | | | | | | | | | |
12‑Mar‑2009 | Indian Wells Masters | Hard | Q2 | 291 | 176 | (21)Rik De Voest [RSA] d. Monroe | 6-3 6-4 | | | | | | | | | |
12‑Mar‑2009 | Indian Wells Masters | Hard | Q1 | 291 | 87 | Monroe d. (3)Evgeny Korolev [KAZ] | 7-6(3) 1-6 6-2 | | | | | | | | | |
2‑Mar‑2009 | USA F6 | Hard | R32 | 292 | 739 | Antonio Ruiz Rosales [MEX] d. (2)Monroe | 6-1 6-2 | | | | | | | | | |
23‑Feb‑2009 | USA F5 | Hard | R32 | 300 | 614 | Alexander Somogyi [SVK] d. (1)Monroe | 1-6 6-4 7-5 | | | | | | | | | |
16‑Feb‑2009 | USA F4 | Hard | F | 298 | 291 | (1)Michael Russell [USA] d. (2)Monroe | 6-2 6-4 | | | | | | | | | |
16‑Feb‑2009 | USA F4 | Hard | SF | 298 | 733 | (2)Monroe d. (Q)Mislav Hizak [CRO] | 2-6 6-4 5-1 RET | | | | | | | | | |
16‑Feb‑2009 | USA F4 | Hard | QF | 298 | 508 | (2)Monroe d. Andrey Kumantsov [RUS] | 6-2 6-2 | | | | | | | | | |
16‑Feb‑2009 | USA F4 | Hard | R16 | 298 | 783 | (2)Monroe d. (Q)Erling Tveit [NOR] | 6-3 7-5 | | | | | | | | | |
16‑Feb‑2009 | USA F4 | Hard | R32 | 298 | 574 | (2)Monroe d. Nikita Kryvonos [USA] | 6-2 7-6(3) | | | | | | | | | |
2‑Feb‑2009 | Mexico F2 | Hard | R32 | 321 | 751 | Mislav Hizak [CRO] d. (1)Monroe | 6-3 6-0 | | | | | | | | | |
26‑Jan‑2009 | Mexico F1 | Hard | F | 316 | 638 | (2)Monroe d. Chris Klingemann [CAN] | 6-3 6-2 | | | | | | | | | |
26‑Jan‑2009 | Mexico F1 | Hard | SF | 316 | 437 | (2)Monroe d. (4)Rafael Arevalo [ESA] | 6-7(6) 6-4 6-2 | | | | | | | | | |
26‑Jan‑2009 | Mexico F1 | Hard | QF | 316 | 740 | (2)Monroe d. Greg Ouellette [USA] | 3-6 7-6(5) 7-6(2) | | | | | | | | | |
26‑Jan‑2009 | Mexico F1 | Hard | R16 | 316 | 530 | (2)Monroe d. (Q)Victor Romero [MEX] | 6-0 6-4 | | | | | | | | | |
26‑Jan‑2009 | Mexico F1 | Hard | R32 | 316 | 794 | (2)Monroe d. Adriano Biasella [ITA] | 6-4 6-2 | | | | | | | | | |
19‑Jan‑2009 | USA F2 | Clay | QF | 316 | 405 | (6)Nicolas Todero [ARG] d. (2)Monroe | 6-7(4) 6-2 6-1 | | | | | | | | | |
19‑Jan‑2009 | USA F2 | Clay | R16 | 316 | 969 | (2)Monroe d. (Q)Rhyne Williams [USA] | 7-6(2) 6-3 | | | | | | | | | |
19‑Jan‑2009 | USA F2 | Clay | R32 | 316 | 761 | (2)Monroe d. (WC)Chase Buchanan [USA] | 7-5 6-1 | | | | | | | | | |
12‑Jan‑2009 | USA F1 | Clay | R32 | 315 | 449 | Michael Mcclune [USA] d. (3)Monroe | 0-6 6-3 7-6(6) | | | | | | | | | |