I am linking "allegro_physfs-5.0.0-RC4-mt.dll", which I assume is the correct file?
1//...
2
3#include <allegro5/allegro.h>
4#include <allegro5/allegro_image.h>
5#include <allegro5/allegro_font.h>
6#include <allegro5/allegro_ttf.h>
7#include <physfs.h>
8#include <allegro5/allegro_physfs.h>
9
10// ...
11
12ALLEGRO_BITMAP *title_screen_bitmap = NULL;
13
14ALLEGRO_FONT *technoid_font = NULL;
15ALLEGRO_FONT *technoid_font_small = NULL;
16
17//...
18
19int main(int argc, char **argv)
20{
21 //...
22 if(!al_init())
23 {
24 cout << "failed to initalize allegro!" << endl;
25 return -1;
26 }
27
28 Cout_Debug_Version_Data();
29
30 if(!al_init_image_addon())
31 {
32 cout << "failed to iniitalize allegro image" << endl;
33 return -1;
34 }
35
36 ALLEGRO_DISPLAY *display = NULL;
37 display = al_create_display(SCREEN_W, SCREEN_H);
38 if(!display)
39 {
40 cout << "failed to create display!" << endl;
41 return -1;
42 }
43
44 if(!PHYSFS_init(argv[0]))
45 {
46 cout << "failed PHYSFS init" << endl;
47 return -1;
48 }
49
50 if(PHYSFS_mount("resources.zip", "/", 1) == 0)
51 {
52 cout << "Could not find resources.zip" << endl;
53 return -1;
54 }
55
56 al_set_physfs_file_interface();
57 al_init_font_addon();
58 al_init_ttf_addon();
59
60 // init other stuff...
61
62 //...
63
64 title_screen_bitmap = al_load_bitmap("title_screen_bitmap.bmp");
65 if(title_screen_bitmap == NULL)
66 {
67 cout << "problems" << endl;
68
69 } // works fine, no problems
70
71 technoid_font = al_load_ttf_font("TECHNOID.ttf",60,0);
72 technoid_font_small = al_load_ttf_font("TECHNOID.ttf",30,0);
73
74 if(technoid_font == NULL || technoid_font_small == NULL)
75 {
76 cout << "text loading failed" << endl;
77 return -1;
78 } //couts text loading fail and quits
79
80// Everything else
81
82}
Edit: I changed to technoid_font_small = al_load_ttf_font("TECHNOIDS.ttf",30,0); and it works. Is it that I cannot load the same file twice? 
Thanks though.