# 2016 Fairfield Challenger – Singles

Taylor Fritz was the defending champion but chose not to defend his title.
Santiago Giraldo won the title after defeating Quentin Halys 4–6, 6–4, 6–2 in the final.

## Seeds

* Frances Tiafoe (second round)
* Santiago Giraldo (champion)
* Tim Smyczek (second round)
* Darian King (first round)
* Alessandro Giannessi (quarterfinals)
* Dennis Novikov (first round)
* Grega Žemlja (quarterfinals)
* Maximilian Marterer (quarterfinals, retired)

## Draw
### Key

* Q = Qualifier
* WC = Wild card
* LL = Lucky loser
* Alt = Alternate
* SE = Special exempt
* PR = Protected ranking
* ITF = ITF entry
* JE = Junior exempt
* w/o = Walkover
* r = Retired
* d = Defaulted
* SR = Special ranking

### Finals

| Semifinals | Semifinals | Semifinals | Semifinals | Final | Final | Final | Final | Final |
| | Quentin Halys | 6 | 6 | | | | | |
| Q | Brydan Klein | 2 | 4 | | | | | |
| Q | Brydan Klein | 2 | 4 | | Quentin Halys | 6 | 4 | 2 |
| | | | | 2 | Santiago Giraldo | 4 | 6 | 6 |
| | Joris De Loore | 3 | 4 | 2 | Santiago Giraldo | 4 | 6 | 6 |
| 2 | Santiago Giraldo | 6 | 6 | | | | | |

### Top half

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Semifinals | Semifinals | Semifinals | Semifinals |
| 1 | F Tiafoe | 7$^8$ | 6 | | | | | | | | | | | | | | | |
| | B Rola | 6$^6$ | 3 | | 1 | F Tiafoe | 2 | 6 | 5 | | | | | | | | | |
| | D Nguyen | 7 | 4 | 2 | | Q Halys | 6 | 4 | 7 | | | | | | | | | |
| | Q Halys | 5 | 6 | 6 | | | | | | | Q Halys | 6 | 0 | | | | | |
| WC | R Opelka | 6 | 6 | | | | | | | 8 | M Marterer | 0 | 0$^r$ | | | | | |
| Q | H Podlipnik | 3 | 1 | | WC | R Opelka | 6 | 6$^4$ | 5 | | | | | | | | | |
| | L Broady | 5 | 4 | | 8 | M Marterer | 3 | 7$^7$ | 7 | | | | | | | | | |
| 8 | M Marterer | 7 | 6 | | | | | | | | | | | | | Q Halys | 6 | 6 |
| 4 | D King | 7 | 5 | 6$^4$ | | | | | | | | | | | Q | B Klein | 2 | 4 |
| | R Bemelmans | 5 | 7 | 7$^7$ | | R Bemelmans | 3 | 7 | 6$^4$ | | | | | | | | | |
| Q | B Klein | 4 | 7 | 7 | Q | B Klein | 6 | 5 | 7$^7$ | | | | | | | | | |
| | T Sandgren | 6 | 5 | 5 | | | | | | Q | B Klein | 7$^7$ | 3 | 6 | | | | |
| WC | T Fawcett | 4 | 1 | | | | | | | | T Paul | 6$^5$ | 6 | 1 | | | | |
| Q | C Norrie | 6 | 6 | | Q | C Norrie | 6 | 3 | 4 | | | | | | | | | |
| | T Paul | 6 | 6 | | | T Paul | 1 | 6 | 6 | | | | | | | | | |
| 6 | D Novikov | 4 | 4 | | | | | | | | | | | | | | | |

### Bottom half

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Semifinals | Semifinals | Semifinals | Semifinals |
| 5 | A Giannessi | 6$^2$ | 7$^8$ | 6 | | | | | | | | | | | | | |
| | J McGee | 7$^7$ | 6$^6$ | 3 | 5 | A Giannessi | 6 | 6 | | | | | | | | | |
| | L Sonego | 6 | 6 | | | L Sonego | 2 | 4 | | | | | | | | | |
| | F Dancevic | 3 | 0 | | | | | | | 5 | A Giannessi | 4 | 1 | | | | |
| WC | K Smith | 6$^2$ | 3 | | | | | | | | J De Loore | 6 | 6 | | | | |
| | J De Loore | 7$^7$ | 6 | | | J De Loore | 6 | 7$^7$ | | | | | | | | | |
| | D Shapovalov | 2 | 4 | | 3 | T Smyczek | 4 | 6$^5$ | | | | | | | | | |
| 3 | T Smyczek | 6 | 6 | | | | | | | | | | | | J De Loore | 3 | 4 |
| 7 | G Žemlja | 7$^7$ | 7$^7$ | | | | | | | | | | | 2 | S Giraldo | 6 | 6 |
| | N Rubin | 6$^2$ | 6$^4$ | | 7 | G Žemlja | 6 | 6 | | | | | | | | | |
| Q | Dennis Nevolo | 6 | 7$^7$ | | Q | D Nevolo | 2 | 3 | | | | | | | | | |
| | S Bangoura | 4 | 6$^5$ | | | | | | | 7 | G Žemlja | 1 | 4 | | | | |
| SE | M McDonald | 3 | 4 | | | | | | | 2 | S Giraldo | 6 | 6 | | | | |
| WC | B Baker | 6 | 6 | | WC | B Baker | 4 | 7 | 4 | | | | | | | | |
| SE | M Mmoh | 3 | 5 | | 2 | S Giraldo | 6 | 5 | 6 | | | | | | | | |
| 2 | S Giraldo | 6 | 7 | | | | | | | | | | | | | | |